Win A Date With Nate Archibald!
by mrschuckbassx3
Summary: Chuck, Blair & Serena are best friends living in Brooklyn. Their lives suddenly change when Blair wins a date with Nate Archibald, the most famous actor of their time! Based on the movie Win a Date with Tad Hamilton! Very AU & slightly OOC. CB, of course!
1. Chapter One

**Okay, so here's my new fan fic! I was watching Win A Date With Tad Hamilton, and thought it'd be cute to make the story for Chuck & Blair! Very AU and OOC, but still lots of CB goodness!! I hope you guys like it, let me know if I should continue!**

**Disclaimer: I do not own Gossip Girl or Win A Date With Tad Hamilton.**

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**Win a Date with Nate Archibald**

**Summary: Chuck, Blair and Serena are best friends living in Brooklyn, New York. Their lives suddenly change when Blair wins a date with Nate Archibald, the most famous actor of their time! Based on the movie Win a Date with Tad Hamilton! AU & OOC. Chuck & Blair, of course.**

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Chapter One

"_Hello Betty," he said in a brooding tone looking at the girl who had broken his heart. "Shouldn't you be at the hospital with a certain other soldier?"he asked._

"_Is there any way you can find it in your heart to forgive me?" Betty pleaded with sad eyes._

"I wonder if these two get together," Chuck Bass whispered sarcastically to his two best friends, Blair Waldorf and Serena Van der Woodsen, as they watched the final scenes of the movie play out on screen.

"Shhhh!" Blair and Serena both hissed back at him trying not to miss a moment of the movie. Chuck rolled his eyes as he couldn't believe how pathetic this movie was. And what was even more pathetic is that his friends were actually buying into it.

"_I'll forgive you on one condition," he said._

"_What's that?" Betty asked, hope in her eyes._

"_Dance with me," he demanded as he reached his hand out for hers. She quickly grabbed his arm and jumped into his arms for a romantic kiss. The danced in the moonlight to the music playing from the car stereo looking as happy as ever._

Blair and Serena both sighed at the unbelievably romantic moment. Chuck just rolled his eyes again, shocked that such a cheesy line made all of these women in the theater swoon. Blair and Serena applauded loudly as the credits began to roll.

"Explain one thing to me. What kind of desperate and pathetic emotional cripple…would actually buy that as an ending?" Chuck asked, still confused as to how such a stupid ending was considered good. He looked over and saw that both Blair and Serena had tears in their eyes and he just rolled his own again. _Of course,"_ he thought, not really surprised that the movie had affected his friends that way.

"Blair, do you think that in real life Nate Archibald is the man that he seems to be on the screen?" Serena asked, completely ignoring Chuck's comment. She was still swooning over the amazing performance that they had just witnessed.

"Oh, absolutely!" Blair responded. "I mean, you can't just fake that kind of thing," she continued.

Serena nodded and took Blair's hand. "What do you think Nate Archibald is doing right now?" she asked.

"I'll bet he's in church," Blair responded squeezing her best friend's hand.

Chuck rolled his eyes again, what is that four times tonight? How foolish could these two girls be? If he were Nate Archibald, the most famous and highest paid movie star of the year, he most certainly would not be in church right now. "You guys are seriously delusional," Chuck said as he began to stand up to exit the theater.

The two girls just rolled their eyes and sighed as they followed their friend out of the theater. When they got outside, Blair realized that it had gotten a little chilly. Chuck immediately noticed her shivering, so he took of his jacket and put it on her shoulders.

"Thanks," Blair said smiling. They walked down the streets of Brooklyn on their usual path after seeing a movie. Serena's apartment building was the first one they hit.

"Okay guys, goodnight! See you at work," Serena said as she made her way up the stairs to let herself into the building.

"Goodnight, S" Blair called after her. Blair and Chuck waited until she got safely into the building before continuing their way home.

****

"That movie was so amazing. I think that was Nate's best performance yet," Blair said, making conversation as they walked hearing the sounds of the city surrounding them.

Chuck rolled his eyes. "Are you kidding me? That movie was as pathetic as all the other movies he's in," he said with a disgusted tone.

"Whatever, Chuck. Just because you don't have a romantic bone in your body doesn't mean you can't enjoy a good chick flick every once and a while," Blair commented.

"Actually, that's exactly what that means," Chuck replied with a smirk on his face.

"Look, you can put that smirk on all you want. I know that somewhere deep down inside you there's a hopeless romantic just waiting to come out," Blair said teasingly. She knew it was true though.

"And what is it waiting for, I wonder," he said playing along.

"I don't know exactly. I think that it's waiting for the right person. Somewhere out there is the girl of your dreams Chuck Bass, and when you meet her, that romantic will want to come out," Blair said.

Chuck didn't say anything. He just looked at his best friend incredulously. _God, she's beautiful, _he thought. If only she knew that maybe she was that girl. But, it was pointless, Blair Waldorf would never settle for Chuck Bass. She deserved much better than that, and Chuck knew it. He immediately shook away his thoughts and responded. "Please, you forget who you're talking to." He was Chuck Bass after all. And Chuck Bass did not have girlfriends. Nor was he romantic. Although, he couldn't help but think that if he did have a girlfriend, and if he was to be romantic with anyone, it would be Blair Waldorf. But he could never tell her that.

"So do you," she shot back. "You forget that I've known you since we were five. That's eighteen years of knowing someone. I know everything there is to know about you, and I know what you could be capable of." Blair knew that if Chuck just let go of all the ridiculous womanizing ways he had gotten himself into after high school, he could make some girl really lucky someday.

_You don't know everything about me, _he thought. _If you did, you'd know that I've been in love with you since we were five. _"Whatever you say, Waldorf," he said throwing her another smirk.

"I know I'm right," she said pointedly. "You just wait Chuck Bass."

****

They continued their walk silently to Blair's house and found her father sitting out on the front porch reading the paper as he always did at night. "There you guys are! How was the movie?"

"Hi daddy," Blair said as she gave him a hug. "It was amazing, of course. Nate Archibald is amazing."

"Always swooning over that Archibald, aren't you sweetie," her father said laughing. "What about you Charles? Did you enjoy the movie?"

"I can't say I liked it as much as Blair here did, Harold," Chuck laughed.

"Well, I figured. You really are a great friend, Charles, always accompanying Blair and Serena to those movies even when they are complete torture for you," Harold said laying a hand on Chuck's shoulder.

"Only for them," Chuck said winking at Blair. She smiled in return. "Well I should get back to the apartment, call it a night."

"Yes, of course. You all have work in the morning don't you?" Harold asked.

"Bright and early, sir," Chuck said getting up from the couch on the porch. "Good night, Harold. Good night, Blair."

"'night Chuck," Blair said as she leaned onto her dad's shoulder.

"Good night, Charles," Harold called after.

When Chuck was out of sight, Harold turned to his daughter. "You really are lucky, you know, to have a friend like Charles."

Blair smiled up at her dad. "Yeah, I am. He's always been there for me."

"You know, you two would make an excellent couple," her father said teasingly. He knew the way Charles looked at his daughter. He liked the boy; he would be good for Blair.

"Dad, it's not like that at all. I've known him forever, he's just a friend," Blair responded almost laughing.

"Alright, alright, I'm just saying."

"Oh, you're just saying, huh?" Blair laughed. "Okay, I'm going to bed. Good night, daddy." She gave him a kiss on the cheek, stood up from the couch and headed inside.

"Good night, sweetheart," he called after her.

****

As Blair got ready for bed, she couldn't help but think about what her dad had said. Her and Chuck a couple? Sure, he had devilish good looks and a charming personality. But he was her best friend, it'd be weird. Besides, he liked to play the field, and Blair was a one man kind of girl. As she turned the light off in her room and got under the covers of her bed, her thoughts immediately went away from Chuck and moved to Nate Archibald. _Boy was he dreamy_, she thought as she drifted off to sleep.

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**What do you guys think? Should I continue? Review please!**


	2. Chapter Two

**I had this chapter written, so I figured why wait to update it? I hope you guys are liking this. Also, I will be updating The Past Matters soon, I promise! **

**This chapter uses a lot of dialogue from the movie! Enjoy!**

**Disclaimer: I do not own Gossip Girl or Win A Date With Tad Hamilton.**

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**Win A Date With Nate Archibald!**

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Chapter Two

"Nate, you don't make this easy on us."

Nate Archibald looked up from his plate wondering what he was talking about. He was out at lunch in L.A. with his agents, Richard Levy and Richard Levy. Yes, they were both Richard Levy, don't ask. He calls one Richard and the other Levy just to avoid confusion. "What do you mean?" he asked confused.

Richard held up a tabloid magazine that had a photo of Nate with a girl in his convertible. The two were drinking and smoking. "This is the shot the paparazzi got," his agent explained. "Congratulations, you're actually drinking, driving, smoking, and groping at the same time."

"Which on the one hand, is just about the coolest thing I've ever seen-" Levy began saying.

"Levy," Richard said in a tone telling him that he was not helping the situation at all.

"-on the other hand, it can be argued that this could be bad for the image," Levy finished.

Nate sighed as he listened to his agents begin to lecture him.

"You play characters that have heart," Richard explained. "This is a person," he continued pointing to the picture, "who would have a heart attack."

Nate sighed and rolled his eyes under his sunglasses. "I can't believe you guys are trying to blame my unemployment on a stupid picture."

"Whoa, whoa, first of all, you are _not_ unemployed," Richard said. "Stock workers are unemployed. You are simply between million dollar paydays."

"And so are we," Levy began, "since we both get a percentage of your payday."

Richard shot him a look.

"But this isn't about us," Levy said trying to save himself from his previous comment.

"Whatever happened to the part in that Jimmy Ing movie? I'm perfect for that," Nate asked confused and annoyed.

"Well, he's taking a breath," Richard explained.

"He's what?" Nate said dumbfounded. This sounded absolutely ridiculous.

"He's taking a breath—pausing before making his decision."

Nate sat back in his chair and ran his hands through his hair. "I don't believe this."

"And you know what Nate, this is only going to make him breath longer," he said, again motioning towards the picture.

"Okay, so what do we do?" Nate asked. He needed to get this part; it's been too long to not have a project lined up. He was starting to get nervous that his days on top were already coming to an end.

"We figure out a way to asphyxiate the son of a bitch," Richard said.

"Find a way to generate a little positive PR," Levy explained, reiterating what Richard had just said.

"What are you an interpreter now?" Richard asked annoyed.

"I'm saying, Nate, that we need to remind Jimmy Ing and the rest of America that you are the boy next door," Levy continued.

"Hey, I am the boy next door," Nate said firmly. "If you happen to live in a very dysfunctional neighborhood," he continued noticing the unconvinced expressions on his agents' faces.

"Alright, I've got an idea. We create a contest. 'Win a date with Nate Archibald'." Levy said.

Nate was a little skeptical. "I don't know Levy, how is that going to improve my image?"

"No, it's perfect. We let some lucky unknown girl win a date with Nate Archibald. It shows that you don't always go for the models or actresses, you go for the real people too." Levy explained enthusiastically. He really liked this idea and really thought it could work.

"We could make it so that donations benefit a charity or something," Nate said trying to build on Levy's idea.

"Perfect! This is perfect. It's just what we need to get Jimmy to stop breathing," Richard said finally on board.

Nate was finally convinced. "Alright, let's set this up then. Get me a date," he said as he held up his glass to toast his agents.

They continued their lunch making small chat about things going on in Hollywood. Nate was listening, but he was really thinking about the contest. _This will work_, he told himself. I'll take out some humble fan, show America that I'm their sweetheart, and then Jimmy will stop breathing and give me the role. _Everything will be back on track in no time,_ he thought.

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**Thoughts? Review please! Next chapter will bring us back to Brooklyn with Blair, Chuck, and Serena!**


	3. Chapter Three

**Here's the next chapter! Thank you so much for the reviews and I'm glad you all are liking it!! My next update will be for The Past Matters, I promise!! Enjoyy!**

**Disclaimer: I do not own Gossip Girl or Win A Date With Tad Hamilton.**

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**Win A Date With Nate Archibald!**

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Chapter Three

The next morning, Chuck, Serena and Blair were sitting in Chuck's office at the Jammin' Java having their morning coffee. Chuck was the manager of the music club/cafe, and every morning before work, Blair and Serena would hang out in Chuck's office, drinking coffee, using his computer or just reading a magazine. It definitely paid to be best friends with the boss.

With about a half hour left until they opened for the day, Blair decided to check her e-mail on Chuck's computer. Chuck was sitting on the couch with his legs propped up on the coffee table in front of it. He was drinking his coffee while reading the entertainment section of the paper. He still needed a band for Friday night, as the one that was originally booked cancelled. Serena was on a lounge chair reading the latest issue of People, which of course, had Nate Archibald on the cover. She was munching on a can of sour cream and onion Pringles. Blair was eating original. Pringles had always been their favorite snack.

"Congratulations," Chuck said looking over at Serena who was shoving large amounts of chips into her mouth at once, "you've officially eaten your body weight in Pringles." He didn't understand how these girls could eat so many damn Pringles and still have it have no effect on them whatsoever.

Serena just rolled her eyes and turned to Blair, ignoring Chuck's snide comments once again. "What's your favorite Pringle? Sour Cream & Onion, or Original?"

Chuck rolled his eyes and went back to reading the paper. He couldn't believe they were having this conversation.

"Well," Blair started, "the Sour Cream & Onion has a very strong taste. So if you're eating a small amount, say…half a can, you want that strength. But if you're eating much more than that, then go with the Original. It's a cleaner flavor."

"Wait until you discover Barbeque flavor," Chuck teased.

"Oh good one, Chuck," Serena said as she went back to her magazine.

They all continued going about their business in silence until Blair let out a scream. "OH. MY. GOD!"

Chuck looked up from his paper and Serena from her magazine. "What is it, B?" she asked, a slight hint of concern in her voice. Chuck also looked concerned.

"Win a date with Nate Archibald!" Blair squealed.

"What?!" Serena threw down the magazine and ran over to the other side of Chuck's desk to look at the computer screen with Blair.

Blair continued to read what she had found on the screen. "Aww, it's to benefit _Save the Children_," she sighed.

"Oh, that is so like him," Serena commented. She always knew Nate Archibald was the man he was on screen.

"Saving the children, I know!" Blair squealed again.

"See, Chuck, Nate Archibald is a saint," Serena said shooting a smirk at her friend.

"Should I enter?" Blair asked excitedly. She knew her chances of winning we slim, but this was Nate Archibald they were talking about. You just can't pass that up.

"Why not," Serena said joining in on her excitement.

"Sure, heaven is just a mouse click away," Chuck teased, still reading his paper.

Ignoring him, Blair kept reading the screen. "A mouse click and a hundred buck donation," she said sadly.

"Oh, well we could raise a hundred bucks," Serena suggested.

The girls looked at each other and smiled. They both were thinking the same thing as they got up from looking at the computer and walked over towards Chuck..

"With your permission, of course, Chuck," Serena said sweetly, as both girls put on their puppy dog faces.

"I'm sorry?" he asked. "You can't be serious." But even as he said it, Chuck knew the answer.

"Of course we're serious Chuck! Come on, do this for me please?" Blair said practically begging.

God he hated how much control she had over him. Chuck Bass just could never say no to Blair Waldorf. "Alright, but no harassing customers. You ask them once and if they refuse move on," he said laying down the rules.

Blair and Serena squealed. "Oh, you're the best Chuck!" Blair leaned over and threw her arms around Chuck giving him a hug.

"Okay, enough playing around. It's time to get to work. We open in five minutes," he said.

Chuck walked out of his office and into the cafe. He went over behind the bar to make sure the coffee machines were on and working, before heading back to the kitchen to make sure the cooks were ready to go for the day. Blair followed him, putting on her apron and pulling the chairs down from on top of the tables. Serena stayed behind to make a jar for donations from customers.

_Blair is so winning this contest,_ Serena thought as she finished the jar and put it next to the register on the bar.

****

The café was pretty busy all day. Chuck stayed working at the register and behind the bar, seeing as how his usual bartender, Angelica, was out of town. Blair and Serena were constantly moving, serving people coffee and food. They both made sure to tell their customers to consider donating to benefit the children when they paid. They were pleasantly surprised to see that many people had been happy to oblige.

When Blair had a free second she went behind the bar to find Chuck. "How are the donations looking?" she asked excitedly.

Chuck rolled his eyes. He didn't really want to talk about the fact that their plan had worked. The jar was completely full, there was no doubt in his mind that they had made the hundred bucks they needed. He hated the fact that he was taking a part in helping the woman that he loved win a date with another guy. And not just a guy, a famous movie star. Not that she would ever win the contest, but still. "See for yourself," he finally said gesturing towards the jar.

Blair jumped up and down in excitement. "We did it, Chuck! I can enter now!"

While she was celebrating she didn't notice that a man in a suit was waiting behind the register. He cleared his throat impatiently.

"Oh, I'm sorry sir, what can I do for you?" Blair asked sweetly, smiling at the customer.

"I'm John Marks. I have a meeting with Chuck Bass," he said.

Chuck, who was sorting things behind the bar, turned around when he heard his name. "Mr. Marks, I am so sorry to keep you waiting. We're a bit understaffed today," Chuck explained extending his hand to the man.

"It's quite alright, I understand. And please, call me John," the man said returning Chuck's handshake.

"Blair could you man the bar for a bit, I'll be in my office," he asked as he led John towards the back of the café.

"Sure, no problem," she responded. Blair was confused. Who was this John Marks guy? And since when did Chuck start taking meetings during business hours? She shook the thoughts away when she realized that Chuck was the owner and manager, of course he had to take meetings. There was sure to be a million things to do, managing a café like this one.

****

"Please, John, have a seat," Chuck said as he sat down behind his desk.

"Thank you, Chuck. Now, as I'm sure you know, Jammin' Java has been doing very well over the past few years, and it's gained a fair amount of popularity here in Brooklyn."

"Thank you, John. I'm very fortunate that the place is doing so well. I've only been the owner for three years, but I've somehow managed to bring this place back to life." Chuck had dropped out of his last year in college after he had come across the abandoned coffee shop. He was always interested in music, and always dreamed of running a café and music club. When the opportunity came along to buy the place and try and resurrect it, Chuck thought the timing couldn't have been more perfect.

"Indeed. And while, it has gained popularity with your customers, it has also gained some attention from some potential clients," John continued.

"Clients?" Chuck asked confused.

"Yes, Chuck. There are many people interested in investing in the place, myself included. Actually, I'm sure many people would be willing to offer a great amount of money to you for ownership," John explained.

"Look, John. I appreciate it, I really do. But this place is my life; I have no interest in selling." Chuck said calmly.

"Of course I understand. But please, take my card. Think it over. I can assure you; this place is worth quite a large sum." John said standing up and reaching into his coat pocket for his card.

Chuck stood up and accepted the card. "Thank you for coming in Mr. Marks," Chuck said walking towards the door. "Please stop and get a coffee on your way out, on the house."

"Thank you, Chuck, and I hope to speak to you in the future."

Chuck watched John walk to the bar to get a coffee. He looked around the café and saw people drinking coffee, eating food, listening to the music and enjoying themselves. _Sell Jammin' Java?_ he thought. No way, he had put way too much time and effort into this place to just sell it to someone else. He loved his job, and he loved who he worked with. Chuck Bass was not selling this place anytime soon.

****

By the time, nine o'clock rolled around, Chuck had almost completely forgotten about his conversation with John Marks. They had been insanely busy today. It was amazing that having just one person gone, made the rest of their jobs so crazy.

"I think we need to hire a new waitress," Blair said as she plopped down on a chair after cleaning her last table.

"I completely agree. Today was so crazy," Serena said sitting down next to her. She had a plate of fries with her that she had gotten from the kitchen.

"And what makes you think that any of that is your decision?" Chuck joked as he joined them, drinking a beer.

"Fine, let me rephrase. Chuck, I think _you_ need to hire a new waitress," Blair said, stealing fries from Serena's plate.

"I couldn't agree more," Chuck said. There was no denying it, today was crazy. And recently most days had been this crazy. Not to mention the weekends when they had bands playing. "I guess I can start looking for someone tomorrow."

"Good," Serena said. "So who was that guy you were meeting with?" She had noticed that Chuck had gone into his office with a tall man in a business suit and was curious.

"Oh, no one. Just someone offering to buy the place," Chuck said as if it was no big deal.

"Wait, what? You're selling Jammin Java?" Blair asked, her voice getting high pitched with shock.

"Are you kidding…no! You know how much I love this place. Mr. Marks just was informing me that this place was getting valuable and that if I was interested, there would be many potential buyers or investors," Chuck explained.

"Well good. Because we love this place too," Serena said, still shoving fries in her mouth. Serena had gone to college, but she still didn't know what she wanted to do with her life. Having this as a job made her really happy. She loved working with her two best friends, and she was able to maintain a stable living doing so. She wasn't ready for any of that to change.

Blair didn't say anything. Sure, she knew how much this place meant to Chuck, but for some reason she couldn't picture him doing this for the rest of his life. He was twenty-three years old for crying out loud. He had dropped out of college for this, but that didn't mean he couldn't go back and get a degree. Chuck was extremely smart; he could do anything he wanted to. Blair hoped Chuck wasn't settling.

"What's on your mind, Waldorf?" Chuck asked, noticing her silence. He could always tell when there was something on her mind.

Blair didn't have the heart to tell him what she was really thinking. What right did she have telling him how she thought he should live his life? "Nothing," she said putting on a smile. She grabbed Chuck's beer and took a large swig. "I just remembered I have to go enter the contest!"

Chuck grabbed his beer back playfully and rolled his eyes. Blair and Serena both ran back into Chuck's office with the tip jar to get on the computer. Chuck went over to split up the tips that everyone had made that night. He laid out a pile for each of his employees and went over to balance the cash register.

He had just finished when Blair and Serena came waltzing out of his office with large smiles on their faces.

"She did it!" Serena squealed. "Now we just wait for you to win!"

"Serena, let's not get our hopes up to high," Blair said, even though she knew they were already really high. "Ready to walk us home, Chuck?"

"Yeah, let me just lock up. Your tips are on the bar," he said walking towards his office.

"Twenty-seven dollars, not bad," Serena said counting the money.

"Not bad at all," Blair agreed.

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**I know the ending sucks, but this chapter was getting far too long! Review pleaseee!**


	4. Chapter Four

**New update! I've had this written for a while, but I wanted to update The Past Matters first. This will be my last update for a couple of days, I'm going out of town, but I promise to try and write as much as possible while I'm away!**

**To clear something up: Blair _did_ go to college with Serena! Sorry I didn't expand on that! **

**THANK YOU SO MUCH FOR ALL THE KIND REVIEWS, YOU GUYS ARE AMAZINGG! ENJOY!**

**Again, I do not own Gossip Girl or Win A Date With Tad Hamilton.**

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Win A Date With Nate Archibald!

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Chapter Four

[Three Weeks Later]

"Angelica, can I see you in my office?" Chuck called out while the girls were closing up for the night.

Angelica practically dropped everything she was holding and ran towards his office.

Blair and Serena laughed. They knew that Angelica had always had a huge crush on Chuck. He knew it too, but he wasn't about to act on it. He wasn't a relationship guy, and if he went out with someone from work, he'd have to see them every day, which was not ideal.

"Yes, Chuck. What is the object of your desire?" she said sensually as she sat down onto the couch.

Chuck shifted in his chair uncomfortably. He hated how she openly flirted with him, since he felt no feelings towards her whatsoever. "Umm, I just wanted to talk to you about the possibility of hiring another bartender for weekends. I wanted your opinion."

"Is that _all_ you wanted Chuck?" she said flirtatiously, lying back on the couch.

"Yes, that's all I wanted…so what do you think?"

She sighed realizing her flirting was doing nothing. "Yeah, a new bartender is a good idea. The weekends have been getting pretty crazy."

"Good, I'll start looking for someone." He had just hired a new waitress, Jessica to help out Blair and Serena. She was doing pretty well so far, no complaints from customers. During that interviewing process, he found some potential bartenders that he could call back for further interviews. "Thanks, Angelica that will be all."

Angelica sighed loudly again and stood up from the couch. She walked towards the door, but stopped before walking out. "You know Chuck, one day, I know that the answer to my question will be 'you, you Angelica are the object of my desire.'"

Chuck shifted uncomfortably. "Okay...but for now...could you just make sure the register is locked up?"

She sighed again with a smile and turned to leave his office.

****

Blair and Serena teased him the whole walk back to Blair's house.

"Oh, Chuck, you are the object of my desire, take me know," Blair breathed as she wrapped her arms around him.

"Ha ha, very funny," he said, not amused by his friends.

"Come on Chuck, you don't even like her the teeniest, tiniest bit?" Serena asked.

"What? No…she's not my type," he said, trying to sound casual.

"Please, girl is your type." Blair shot back. She had seen him date every type of girl, and she didn't understand why he wouldnt give Angelica a chance. Yeah, she was a little over the top, but she had a good heart.

As they got closer to Blair's house, they noticed a lot of commotion on her front lawn.

"Who the heck are they?" Serena asked.

"Oh no…if that fire alarm went off again…" Blair sighed as they picked up the pace to her house.

"Why would they send a news crew for that?" Chuck asked suspiciously. Now they were getting worried. Had something happened to Harold?

That's when it clicked. "Wait a second…" Blair breathed.

"OH MY GOD, NO WAY!" Serena said as she realized what Blair was thinking.

They ran up towards the house and were bombarded with reporters.

"…how does it feel to be the winner of Nate Archibald's contest…"

"…how long have you been a fan…"

"…Blair, what's your sign? Nate's a Leo…"

_I cannot believe this is happening!_ Blair thought as she heard numerous reporters throw millions of questions her way.

"Blair Waldorf, congratulations! You've won the Win a Date with Nate Archibald contest! I'm Larry Fox, the supervisor for the contest," a man that had approached Blair said.

"OH MY GOD!" Blair screamed. Serena ran next to her and threw her arms around her best friend. They began jumping up and down screaming with delight.

Chuck slowly made his way up to the house. He couldn't believe it. Blair had actually won. Blair was going on a date with Nate Archibald. Nate fucking Archibald. The movie star. Shit. As all of the excitement surrounded Blair, Chuck couldn't help but feel that their lives as they knew them were about to change.

****

A week later, Chuck and Serena found themselves in the airport watching Blair get ready to board her plane to L.A.

Serena couldn't have been happier for her best friend. This was every girl's dream come true. She got to go on a date with Nate Archibald! _She might even kiss him…or maybe even more_, she thought. But Serena immediately shook that thought away. She may be that type of girl but Blair certainly wasn't. She was still a virgin and there was no way she was going to give it up to Nate Archibald who she'd never see again. She was waiting for love and all that romantic stuff.

Chuck still couldn't believe this was actually happening to him. The girl of his dreams was jet setting off to L.A. to go on a date with the most famous movie star…ever. What he was most concerned of was what she was going to do with him. Would she kiss him? Sleep with him? Chuck shuddered at the thought. Blair was still a virgin and deep down he always wanted to be her first. He hoped that she was still serious about waiting for the right person. Even if it wasn't Chuck, it better not be fucking Nate Archibald.

"They also told me, that on the plane you get your own personal DVD player and you get to view the film of your choice," Blair said, telling them all about the rock star treatment she was getting.

"Okay…I would like to touch intimately the person who thought of that," Serena said seriously.

Chuck looked at her with a weirded out face, and Blair just laughed at her friend.

"_Ladies and gentlemen at this time we'd like to begin boarding our first class passengers…" _they heard over the intercom system.

"That's you!" Serena screamed, throwing her arms around her best friend.

"That's me!" Blair squealed with the same excitement.

Chuck rolled his eyes. "Guys, guys, please," he said covering his ears. He didn't know how much more of this squealing he could take.

"Oh Chuck, just give me a hug and tell me to have a good time, please?" Blair said opening her arms up.

Chuck sighed. "Okay," he breathed leaning into Blair's waiting arms. He squeezed her tight, not really wanting to let go. He slowly pulled away. "Just…you know…be careful, okay?"

"What do you mean?" Blair asked confused. It's not like she was going on a jungle safari into the Amazon or climbing Mt. Everest. She was going to L.A. for one night.

"I mean, that this guy is Nate Archibald. In his life…he's probably slept with like hundreds of women," he said.

"No way," Blair said shocked. "That's not even... physically possible. Besides, like he's going to be interested in me that way."

Chuck sighed. God she could be so naïve sometimes. And how could she not think that Nate Archibald wouldn't be interested in her. She was the most beautiful woman in the world; any guy would go crazy for her. "Fine, here's how you know. If at any point in your date, he claims that he doesn't really like watching sports, then he's just trying to sleep with you."

"Okay…" said Blair, a little skeptical. This sounded ridiculous, especially coming from Chuck who goes through different women each week.

"Oh, and if he says he loves animals…then he's _really _trying to sleep with you."

"Okay Chuck…"

"Guys are guys, Blair. Rich or poor. Famous or…coffeemakers…" he said.

"Right, got it Chuck." Blair was still surprised to be getting this speech from Chuck Bass.

"Just do me one thing…" he said moving closer so that he could whisper. "Guard your…carnal treasure."

"Okay," Blair said embarrassed.

"No I just…guard your carnal treasure," he said again, also getting uncomfortable.

"Thanks Chuck," Blair said trying to shake off the awkwardness of the situation.

Serena rolled her eyes at Chuck and interjected the awkward moment. "Remember _everything_, B."

"I will," Blair smiled.

"Remember how he smells…" Serena sighed.

"Oh, I will," Blair squealed.

"No, but not just a vague description, I want good solid similes…for example, 'he smells like a forest on the first day of spring'…"

Chuck rolled his eyes. "Okay, Blair, you better get on the plane," he said trying to end the conversation about Nate Archibald's smell.

"I will bring you similes," Blair told her best friend before turning to the flight attendant with her ticket.

"Oh, wait I almost forgot," Chuck said reaching into his back pocket.

Blair looked down and saw him holding a box of Pringles.

"I got you something…its regular flavor…you know in case you don't like the…prime rib in first class…" Chuck said nervously. He suddenly felt really stupid. Why would she want Pringles when she had all of the food in first class?

Blair smiled and took the can. "Thank you, Chuck." She turned and gave her ticket to the flight attendant and put her bag through the security belt.

"Just…guard your carnal treasure!" Chuck yelled after her. God what was wrong with him?

"I heard you Chuck!" Blair hissed back, extremely embarrassed. Why was he doing this to her now?

Serena gave Chuck a look. She always had a feeling that Chuck cared about Blair as more than just friends, and this embarrassing display of emotions definitely boosted her theory. She shrugged it off and turned to wave to Blair.

"Bye B!" she called, as she and Chuck watched Blair disappear onto the plane.

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**What do you guys think?! Let me knowwww!**


	5. Chapter Five

**A/N: Finally, an update! I know it's been wayyy to long and I apologize. Things have been so hectic with school starting and trying to update The Past Matters. Thank you so much for sticking with this and thanks for the amazing reviews! This one is a little longer, so hope that makes up for the wait. Enjoy!**

**I DO NOT OWN GOSSIP GIRL OR WIN A DATE WITH TAD HAMILTON!**

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**WIN A DATE WITH NATE ARCHIBALD**Chapter Five

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Several hours later, Blair found herself walking off the plane into Los Angeles International Airport. The excitement that washed over her as she made her way towards the exit of the terminal increased exponentially when she saw a man in a black suit and hat standing with a sign reading 'Ms. Waldorf'.

"Hi, I'm Blair Waldorf," she greeted the man extending her hand to shake his.

"It's a pleasure to meet you Miss Waldorf; welcome to Los Angeles. I'm Andrew your driver for the evening. Please follow me, and allow me to carry your bag for you," the man replied reaching out to take her carry on suitcase.

"Oh no, I can carry it," she said feeling slightly awkward having him carry her bags for her.

"Nonsense, Miss Waldorf, please, I insist."Andrew said with a smile.

Blair allowed Andrew to take her bag and followed him as he led her out of the terminal. She felt very strange having someone do everything for her, but she couldn't deny that she liked it. The whole experience got even better when she realized that she would be driven around in a limo all day. She had been in a limo once before, but it was cheap and rundown and nothing like the beautiful black stretch limo in front of her.

"Miss Waldorf, I will take you on a scenic tour to your hotel so that you can see some of Los Angeles. I have been told to inform you that Mr. Archibald will be arriving at your room at 7:30 this evening for your dinner at 8," Andrew said from the driver's seat as Blair made herself comfortable in the back.

She looked down at her watch. It was 2:30 now, so she had plenty of time to see the sights and still have time to get ready. "Great, thank you Andrew."

Blair sat back in the seat and smiled at the current situation she was in. In less than six hours, she would be on a date with Nate Archibald. Until then, she looked out the window and let herself enjoy her tour of the city.

****

"So what's this girl's name again? Claire?" Nate asked his agents. They were in his closet in his house picking out something for Nate to wear on the date.

"Actually it's Blair. Blair Waldorf," Richard corrected him as he went through Nate's tie collection.

"Blair, right," Nate said as he tore off the current shirt he was trying on in order to try on a different one.

"Remember Nate, this is a big night for you. It's your chance to regain your boy-next door image with the press. So you have to look perfect and this date has to go perfect, understood?" Richard asked him as he held up several ties under Nate's chin.

"Yeah, I got it." Nate said slightly aggravated. It was only the hundredth time he had been reminded.

"Good, because this girl is wholesome- the perfect person to bring up your image," Levy said as he tried on a pair of Nate's shoes. "By the way can I keep these?"

"No," Nate said rolling his eyes, "okay, so I take this girl out, smile for the cameras and then she goes back to wherever she's from and I move on with my life, right?"

"Exactly. That's why this plan is so perfect. You'll never have to see her again," Richard said. "And by the way, she's from Brooklyn, just so you know."

"Right, Blair Waldorf from Brooklyn. This will be _great._" He said as he went back to trying on clothes. "By the way, what about Jimmy Ing? Have we heard anything about that?"

"No, he's still breathing," Richard said solemnly.

"Okay, because I passed Ashton Kutcher in his car today and he seemed pretty happy about something," Nate said, a little skeptical about the situation.

"He's happy for other reasons. I'm sorry but we haven't heard from Jimmy. But trust me, after this girl-next-door date hits the media, everyone will see what a great guy you are," Richard explained.

"And he'll finally stop breathing," Nate finished.

"He'll finally stop breathing." Richard agreed.

****

After arriving at the hotel and being escorted to her celebrity suite, Blair could still not believe what was happening. The hotel room was beautiful with a living room area, a large bed, and a gigantic bathroom. She didn't want to even think about how much staying in a place like this would cost her normally.

At around 7:20, Blair sat at the vanity looking at herself in the mirror. She had chosen a royal blue dress that ended right above her knees. She wore her hair down with a headband that matched her dress. Her shoes were strappy sandals with just enough heel. She was incredibly nervous and was planning on what she should say when she first met the man of her dreams.

"It's very nice to meet you, Nate."

"So nice to meet you Nate."

"It's so great to meet you."

"Your films will stand the test of time."

Suddenly Blair heard a knock on the door and let out a quick gasp. _This is it_, she thought. _I'm going on a date with Nate Archibald!_ She stood up from the vanity and took one last look in the mirror before making her way towards the door. Taking a deep breath, she slowly opened the door. Seeing him standing there, Blair couldn't help but hang her mouth open, gaping at the beautiful man standing before her. She suddenly became even more nervous then she was before and was rendered speechless.

Nate was slightly taken aback by the girl standing in the doorway. She was much more attractive than he had expected from a girl from Brooklyn. She was absolutely stunning. "Hi, I'm Nate," he said smiling, extending his hand to greet her.

Blair looked down at his extended hand and slowly reached out to grab it. Her heart felt like it was going to explode in her chest, she didn't know what to do or say. "Your standing films will time and test themselves," she said, not realizing that she had made absolutely no sense.

Nate shook his head slightly in confusion. "Um, thank you. You look very pretty."

Blair let out a nervous laugh. _Nate Archibald thinks I'm pretty. _This had to be a dream.

"It's Claire, right?" Nate asked.

Blair didn't say anything and just shook her head slightly.

"I'm sorry, what is it?"

"Blair," she breathed out.

"Right, Blair. Nice to meet you. So you ready to go?"

"Yes, thank you," Blair said, finally starting to sound like a normal person.

Nate still looked at her a little strangely and waited for her to follow him out to his limo. Blair followed him still gaping at the man she was with. As they walked out of the hotel, Nate tried to make some friendly conversation.

"So, how was your flight?"

"Your films will stand the test of time," Blair said, just as she had practiced.

"Ah," Nate said. _Well this is going well._ _The girl can barely form a sentence._ "Thank you."

The finally made it to the entrance of the hotel. Nate stopped before opening to doors and turned to Blair. "So, are you ready?"

"For what?" Blair asked confused.

"Right this way," he responded as he put an arm around the small of her back to gently guide her through the doorway.

As they turned to corner, Blair was immediately blinded by hundreds of flashing lights. There was paparazzi everywhere, trying to get a picture of the two leaving for their date. Blair was a little bit overwhelmed and was lucky to have Nate guiding her along as they made their way out to the limo.

"It'll take a few minutes for the spots in your eyes to go away, but trust me they will." Nate said as he guided her into the limo.

"OK," was all Blair managed to say.

Blair sat on the side seat of the limo, while Nate sat in the back. She watched him as he opened the window slightly and lit a cigarette. It made her a little uncomfortable that he was smoking so close to her, but this was Nate Archibald. She wasn't going to say anything.

"So, is it always like that?" Blair asked referring to the massive hoards of paparazzi.

"Yeah, pretty much," Nate said laughing.

"Wow," Blair said as she tried to imagine having to go through that every time she left the house.

"Yeah. So, are you excited?" Nate asked a little smugly, but Blair was to lovestruck to notice.

"Are you kidding? This is like a fairytale," she said smiling.

"Yeah, I figured," he replied.

Suddenly Blair started feeling a little dizzy. She took a deep breath and closed her eyes. As she moved her hand to her head, Nate noticed something was wrong.

"You OK?" he asked slightly concerned.

"What? Oh, yeah. I'm just not used to sitting sideways like this. We don't usually have sideways seating in Brooklyn. And I think that the cigarette smoke is kind of—" she started to explain.

"Well, you can come sit back here if you'd like," Nate offered lamely, still smoking his cigarette.

"Uh…I can't really move right now," Blair said looking down at the floor. She _really _didn't feel too good. "Wow, I don't feel well. I've kinda always been motion sickness-y. Once this carnival came to Brooklyn, and they had that ride where it spins around and you have to stand against the side and the center falls out…and I…" she was rambling trying to ignore the fact that her stomach was turning inside out.

Nate was hardly paying attention, being more concerned that a little bit of ash from his cigarette had gotten on his suit. "Damn it," he muttered brushing it off.

"Um, pardon me," Blair said as she proceeded to vomit all over the floor of the limo.

"Ahhh," Nate exclaimed as he lifted his feet to protect his shoes. He looked down and as the smell hit him started to gag. _This is a disaster_, he thought to himself.

****

Blair, Nate, and Andrew stood outside the limo looking into the back seat.

Blair was extremely embarrassed. "This is just so far from the way I imagined the evening going," she said nervously, trying to lighten the mood.

"No, uh, I mean, it's perfectly all right. Right Andrew?" Nate said looking to his driver.

"Perfectly all right," Andrew agreed, however Blair wasn't convince.

Nate turned to Blair. "Shall we?" he asked extending his arm out to her.

She linked her arm with his and followed him inside the restaurant.

"Good to see you Mr. Archibald," the maitre'd greeted them.

"You too, Michael." Nate responded.

"Hey man, how are you," a person standing by the bar called out as they walked by.

"Good, how are you," Nate replied.

"Hi, Nate!" some girls sitting at a table called out.

"Ladies," Nate greeted smiling. He put his arm around Blair and led them to his usual table. Blair felt a little uncomfortable at the amount of attention he had been getting.

As they sat down, Blair noticed the huge grin that she realized hadn't left his face since they had the run-in with the paparazzi.

"Doesn't it hurt? Smiling like that all the time?" she asked.

"Well, you get used to it," he replied, losing some of the fake grin.

"Should I do it?" she asked curiously.

"Yeah, sure." Nate said. "You might not be able to hold it for very long, but go for it."

Blair placed the biggest smile she could muster on her face and just looked at Nate. Nate just smiled back, knowing that soon she would start to feel it.

"See that, starts to get you right there," he said pointing to his cheeks.

"That's horrible," she laughed as she put her hands on her cheeks.

"I told you," he laughed back. He began pulling his cell phone, his pager, and his Blackberry and placed them on the table.

"You sure have a lot of stuff," Blair commented, finding it a little ridiculous to have that many forms of communication on you at one time.

"Yeah, sorry. I have to make sure I'm never out of touch with the people who torment me," he joked.

"Who are they?" she asked with a concerned tone.

"Agents, managers, people like that," he said as he checked his beeping Blackberry. "This man Jimmy Ing, who's making this movie I'm exactly right for, but, but for whatever reason, he's taking a breath."

"A what?" she asked confused.

"He's thinking it over," he explained.

"Oh," she replied.

"It's just all very competitive, this business, that's all," he continued. "Everybody seems to be chasing the same thing. The same parts in the same movies, the same awards, the same big money."

"Well I'm sure you have too much common sense to get caught up in all that," she said, still convinced that Nate Archibald wasn't one of _those_ Hollywood types. "I mean, it's just a recipe for an unsatisfying life."

Nate looked at her incredulously. What was she saying… that he was some pathetic guy who only cares about the money? Well, he did care about the money, but she was right, he shouldn't be caught up in all that. It should be about the acting, right?

"Obviously you have your priorities straight, so…" she continued.

"So, what do you do Blair?" Nate asked, trying to change the subject. Her words were still making him very confused.

"Oh I work at Jammin' Java," she said happily. She loved her job and talking about it always brought a smile to her face.

"I'm sorry?" Nate asked, not knowing what she was talking about.

"It's a coffee shop and music café," she explained.

"Ah," he said.

"I wait tables," she said.

"Cool," he replied, trying to sound as interested as possible.

"Yeah, I absolutely love it. My two best friends work there, so. It's a lot of fun."

"No, it sounds it," Nate said quickly.

The conversation suddenly started to die. Nate started looking around at other people in the restaurant so Blair tried to think of something to say.

"So, um, what do you do Nate?" she asked before realizing what a stupid question that was.

Nate looked at her a little confused before they both started laughing.

"Oops. What I mean is, what do you do…when you're not doing what you do?" she recovered.

"Not a lot, you know. There's not a lot of time left for hobbies, really. And I don't really like watching sports, so I read," he began explaining.

Blair shifted uncomfortably in her seat, remembering what Chuck had said to her before she left.

"I play with my dog, my cat, my bird, you know. I…I love animals, you know?"

There it was again, Chuck's voice in the back of her head. _"He's just trying to sleep with you."_

"Right," Blair said, a little put off by what was coming out of Nate's mouth.

****

Meanwhile, Chuck and Serena sat at the bar, while Jessica finished helping the few remaining customers in the café.

"What do you think they're doing right now?" Chuck asked as he took a huge swig from his beer. He didn't really want to be thinking about it, but was hoping Serena would make him feel a little bit better about it.

"I bet they're in her hotel room, straining for breath. His manhood…yearning to be free. Her hands running over the ripples in his abdomen. Her perfect bosom…crying out in ecstasy," Serena imagined, although this was really just one of her own fantasies she was recounting.

Chuck just stared at her, hoping to God none of that was true. "Great," he muttered.

****

The evening continued to run pretty smoothly once they had changed the subject from Nate's supposed hobbies, to Blair's life in Brooklyn. When their food had arrived, Blair realized she still had her retainer in, so she pulled it out of her mouth and placed in on the table.

Nate stared at it for a second, then looked back up at her. "I had one of those," he commented.

"A retainer?" she asked.

"Yeah, on the bottoms, and a night brace on the uppers," he explained. "I had really bad teeth as a kid."

"Yeah, I'm sure you were a real ugly duckling," she responded sarcastically.

"I was like anybody else, a little gawky, unsure who I was. Combination skin," he laughed.

"Well you came together nicely," Blair said also laughing.

"Thank you," he replied with a huge grin on his face. "So did you," he said, and he meant it. Sure she was different then they girls in L.A., but there was no denying that she was beautiful.

Blair blushed and continued to eat her meal. Nate just smiled, watching her eat.

****

The rest of dinner went extremely well, the conversation became less awkward and less forced. Blair learned about Nate's childhood and he learned more about Blair's. When the limo driver pulled up, they got in the car, both sitting in the back to avoid a repeat of earlier in the evening.

"So, listen, I can have Andrew take us back to your hotel, and we can call it a night. Or, you could come back to my place, you know…to see the house and stuff." Nate suggested.

Blair blushed and looked up at him. She knew what he was really saying by suggesting they go back to his place. She couldn't believe it all was happening. "Umm, sure, for a little bit."

"Okay," Nate said smiling.

His house was beyond amazing. They walked around back and entered through the back door, leading to his kitchen.

"Wow," she said looking around.

"You like it?" he asked.

"It's amazing," she responded.

Nate walked around the bar in the kitchen and reached for two glasses. He walked over to the liquor cabinet and pulled out a bottle of champagne. "Miss Ramirez? Sonja? Anybody in the casa?" he called out. There was no response. He turned to Blair and handed her a glass. "Guess we're all alone," he said.

"Oh," Blair said. Suddenly she felt like she had made a mistake agreeing to come to his house. She didn't know why she felt so uncertain. This was Nate Archibald's house she was standing in, offering her champagne and probably much, much more. But, she still felt like it wasn't right. She was still a virgin and she wanted her first time to be special. Sure, Nate Archibald is special, but she had just met him. She couldn't sleep with someone she had just met. Chuck's words kept coming back into her brain. _"Guard your carnal treasure," _he had said.

"Umm, actually I'm pretty exhausted. Maybe it's best you just took me back to my hotel."

Nate looked slightly defeated but recovered quickly. "Oh, yeah sure. I understand," he said trying not to sound too disappointed.

"Thanks," she said smiling and then turned to look out the window at the city at night.

When they arrived back at the hotel, Nate got out walking Blair back up to her suite.

"Well, I had a really great time tonight," he said sincerely. He had actually been surprised by the fact that she was such a beautiful woman, inside and out.

"Yeah, me too," she said smiling standing in her doorway.

"It was really great to meet you. I wish you great happiness in life," he said.

"And to you, too," she returned. "Thank you for the best night of my life," she said sincerely.

"No, thank you."

Blair shifted uncomfortably and looked down at her hands not knowing what to do next.

"May I give you a kiss goodnight?" he asked, breaking the silence.

"Oh I think that you might…maybe…may," she smiled, looking back up to him.

Nate smiled back and slowly leaned forward to capture her lips. It was an innocent enough kiss, very sweet and tender. Blair couldn't believe that she had just kissed Nate Archibald. Serena was going to flip when she found out.

"Good night, Nate," Blair said smiling as she slowly backed up into her room and shut the door.

"Good night, Blair. Sweet dreams."

Blair shut the door all the way before standing against it, leaning her head back. She couldn't stop smiling. She had just gone on the most perfect date, with the most perfect man in the world. Slightly disappointed that it was all over, Blair couldn't wait to get home and tell her friends all about it.

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**REVIEW PLEASE! The Past Matters will be updated before I update this one next, just FYI. But i'm working on both I promise!**


	6. Chapter Six

**Sorry it took so long, but here's the next update! Thank you all so much for the amazing reviews, especially EmilyEcstatic---you've been my biggest motivator to keep writing!**

**I'm still working on the epilogue for my other story, The Past Matters, for those of you who read it, so look out for that soon!**

**I do not own Gossip Girl or Win A Date With Tad Hamilton.**

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Win A Date With Nate Archibald

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Chapter Six

"…I began to close the door, I took one last look to see Nate's retreating form, I closed the door, and I finally got into bed," Blair finished recounting her experience to Serena and Chuck during the short break that they usually got before the lunch rush.

"Please tell me you're done," Chuck said rolling his eyes. He really was getting tired of hearing Blair's perfect night with Nate Archibald.

"Yes, Chuck. My story ends there," Blair said with a sigh.

"I cannot remember a time…before you started telling that story," Chuck said, half jokingly.

"Charles, I was asked to give a detailed description of my night, and that's what I did," Blair said curtly. She was annoyed that he was being so rude about the whole thing.

"And you did, you're right, I'm sorry," he apologized honestly. He didn't want to make her upset with him. Especially after the meeting he had yesterday with John Marks.

"_Chuck, thanks for meeting with me again," John Marks said as he took a seat in Chuck's office._

"_It's really no problem," Chuck responded, although he didn't really know what John Marks was doing there. He had already made clear his feelings about selling the place._

"_Look, I know that after our last conversation, this place means a lot to you, and I understand completely. But Chuck, you have a great business going on here, so good in fact, I really think you should consider expansion," John explained._

"_Expansion?"_

"_Chuck, places like this just don't exist anymore, and I want to change that. I'm looking to invest in a place in the city that I'm hoping we could turn into a place like Jammin' Java," John explained._

_Chuck was confused. What did all of this have to do with him? "I'm sorry John, I just don't understand why you need to discuss all of this with me. If you're worried about me suing you or something…"_

"_No, no it's nothing like that. I'm here because I want you to open up the new place. I want you to run it," John clarified._

"_You want me to open a new club in New York City?" _

"_That's exactly what I want. You've obviously done something right with this place; I think you're the perfect guy to do it."_

_Chuck was shocked. He didn't know how to respond. Of course it was an amazing offer, opening a club in the city. It's what he's always wanted to do. But this would change everything. "Look John, that is an amazing offer, but I don't know. I'd have to move to the city to really be close enough to deal with everything, but my life is here…in Brooklyn."_

"_I understand but think of the opportunity Chuck; the city has a much bigger market. The club could be bigger, have much larger musical acts, make a lot more money then you are here. And I understand Brooklyn is your home, but what's really keeping you here besides this place?"_

_Chuck immediately thought of Blair. She was everything to him, and he couldn't imagine his life without her. And Serena, she was one of his best friends and he cared about her greatly. "There are…some people here, I'm not sure I'm prepared to leave behind," Chuck explained._

"_Of course, but Chuck, you're twenty-three years old. You have so much ahead of you. Opening this club in the city could just be the first step, D.C, L.A., you name it. But I think what's important is opening in the city and making it as successful as this one, and even more so. And honestly, you are the only person who could do that. I'm prepared to fully invest in its opening but give you full control of operations. I would keep a small portion of the profits, but virtually the place would be yours to run."_

"_It sounds amazing, John trust me. I just don't know," Chuck said still unsure. The opportunity was incredible. This type of thing was his dream, and New York City was the perfect place. _

"_Think about it, please Chuck. Think about where your life is headed here, and think about what it could be. I'll be in touch," John said as he stood up to leave Chuck's office._

"_I will, thank you," Chuck said shaking his hand and leading him out. _

_When John had left, Chuck slumped into his couch, a million thoughts going on in his head. New York City. Jammin Java in New York City. It was his dream, the opportunity of a lifetime. But what about Blair? He didn't want to leave her in Brooklyn, especially if she didn't know how he felt about her. Chuck sat up as a new thought came into his head. I could ask her to come with me. I could tell her how I feel and tell her to come with me. _

"Actually, Blair, there is something I wanted to talk to you about, it's kind of important," Chuck said as he moved his chair closer to her.

"Sure, what's up?" Blair asked curiously.

Serena scooted closer in her chair to become more part of the conversation. Chuck cleared his throat and stared at Serena hoping she would take the hint. He wanted to talk to Blair…alone.

Serena caught on pretty quickly. "Right…well, I'm going to go check the kitchen," she said excusing herself from the room.

When Serena had finally left the room, Chuck turned back to Blair, a nervous feeling in the pit of his stomach. "So yesterday, I had a meeting with John Marks," Chuck started.

"Another meeting? What did he want this time? I thought you told him you weren't interested in selling," Blair asked confused.

"Yeah actually, he wants to invest in a new Jammin' Java, in the city."

"Jammin' Java in New York city? Chuck, that's amazing!" Blair exclaimed, a huge smile on her face.

"Yeah, and he wants me to be the one to open it and run it…" Chuck explained before trailing off a bit. He wasn't exactly sure how to word the fact that he'd be moving out of Brooklyn.

"You're moving to the city?"

"Look, Blair I've thought a lot about this. This club is my dream, but can you imagine what I could do in the city? It would have so much more potential," Chuck explained.

"No Chuck, that's amazing, really. I'm so happy for you. I just can't believe you're moving!"

"Yeah actually, that's what I wanted to talk to you about. I was kind of wondering if maybe…" he started but was cut off by the sound of his office door opening. He looked up to see who had just walked in and interrupted the most important moment of his life and he couldn't believe his eyes. Nate Archibald. Nate fucking Archibald was standing in his office. Chuck looked down and sighed. He couldn't believe this was happening to him, now of all times. "What's the worst thing…that could possibly happen to me…right now?" he finally said to Blair.

"What?" Blair asked confused. What was he talking about?

"Hey," Nate said, causing Blair to twirl around in her seat and let out a gasp.

"Oh my god, what are you doing here?" she asked, extremely surprised.

"I actually came to see you; I was hoping we could go to lunch or something," Nate began a little nervously.

"Um…yeah of course. Wow, I can't believe you're here," Blair exclaimed standing up and moving towards him to give him a hug.

"Yeah, it's amazing," Chuck said sarcastically.

"Oh gosh, sorry. Nate this is my best friend Chuck Bass. Chuck, Nate Archibald."

"Nice to meet you man," Nate said extending his hand in greeting. "Blair's told me so much about you."

Chuck returned the handshake. "Yeah, you too."

Serena walked back into the office right then carrying a tray of coffee. When she saw who was standing in the room, she let out a yelp and dropped everything she was carrying.

"Nice, Serena," Chuck groaned looking at the mess on his floor.

Serena ignored him and moved towards where Nate and Blair were standing.

"Hello, hi, I'm Serena…Van der Woodsen, Blair's best friend," Serena said extending her arm to Nate and shaking his hand enthusiastically.

"Serena, so nice to meet you. I'm Nate. Blair's told me a lot about you," Nate said sweetly.

Serena was a little hesitant to let go of his hand, but when she saw Blair's annoyed look she finally relented. "Wow, I can't believe Nate Archibald is standing in our coffee shop in Brooklyn!" she thought out loud.

"Yeah, it is a little strange, isn't it?" Chuck said as he began picking up the tray and coffee cups Serena had left on the floor. "What could you possibly have to do in Brooklyn?"

"Yeah, I'll admit it's a little out of my way," Nate explained.

"You mean you're normal itinerary doesn't include coffee shops in Brooklyn, New York?" Serena said sarcastically.

"Not really," Nate laughed. "I wanted to see Blair, there are some things I wanted to talk to her about."

"Well, I'm so glad you're here," Blair said. "And if you let me just grab my stuff we can go find somewhere to eat."

"Um, Blair?" Chuck interrupted. There was no way he was going to let her go off with Nate Archibald. "Aren't you forgetting something?"

"What?" Blair asked pulling on her jacket and rearranging stuff in her purse.

"It's the middle of the day. You can't leave, I need you to work," Chuck said.

"Oh… that's okay, I can come back later," Nate suggested.

"No Nate, it's fine. Chuck, you have Serena, Jessica and Angelica. Plus, you could take a few tables. We'll only be gone a few hours," Blair said.

"Blair, you need to stay," Chuck said firmly. He really didn't want her leaving, especially when he was trying to have a very important conversation with her.

"Chuck, I'm going. We'll be back soon," she said as she threw her purse over her shoulder and grabbed Nate's hand leading him towards the door.

"Have fun guys!" Serena called after them as they made their way out of the café.

"Thanks, and don't worry Chuck, I'll have her back soon," Nate said as he threw somewhat of a smug look in Chuck's direction.

When they were gone, Serena turned back to Chuck. "Oh my gosh, can you believe that just happened? Nate Archibald just flew from L.A just to see Blair! A day after their date! This is so amazing!" she exclaimed as she jumped around Chuck's office in excitement.

Chuck slumped into his desk chair and ran his hand over his face and into his hair. He knew that Nate probably wouldn't stay long, but he couldn't shake the feeling that Nate being here was going to be a bad thing. "Yeah…amazing," he sighed as he got up to clear off some tables.

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**What do you think?! Review please!!**


	7. Chapter Seven

**Okay this story is officially off hiatus! Now that I am down with finals and off of school for the next month, I can focus on writing! I am so sorry for taking so long to update, but I've been so busy! Thanks to all of you that stick with me! So anyways, here is the next chapter, enjoy!**

**I do not own Gossip Girl or Win a Date With Tad Hamilton!**

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**Win A Date With Nate Archibald!**

Chapter Seven

Nate and Blair walked out of the coffee shop and headed towards his car, which was a navy blue convertible that looked way too nice to be driven around on the streets of Brooklyn.

"Wow, nice car," Blair commented as Nate opened the door for her.

"Thanks, I asked the guy at the rental place for a convertible and he gave me his wife's car," he said getting into the driver's seat.

Blair laughed at his joke until she realized he was serious. "Wait, really?"

Nate just smiled and put on his sunglasses before starting up the car and pulling out of the parking space.

Chuck and Serena watched them leave from the window of the café.

"And that is the last time we ever saw her," Serena sighed.

Chuck scoffed and looked at his best friend. "Serena, he's not her type," Chuck stated as if he was trying to convince himself more than Serena.

"No, rich, famous, handsome, ass like cement…you are absolutely right," Serena commented sarcastically. "Please, Chuck…he's like the ultimate dream guy and 100% Blair's type," she added before leaving the window to get back to work.

Chuck clenched his jaw before following Serena's lead.

***

On the way to the restaurant, Blair realized that she and Chuck had been in a pretty important conversation before she left. She felt kind of guilty just leaving so suddenly like that when Chuck was trying to talk to her. She sent him a quick text to check in.

**Hey, wasn't there something you were trying to ask me before I left? –B**

Not a minute later, she received her reply.

**Forget it, it was nothing. Have fun. –C**

Blair closed her phone, accepting Chuck's answer. She still felt like there was something he wasn't telling her, but she wasn't going to worry about it now. She was on her way to a second date with Nate Archibald.

"So where should we go?" Nate asked. "You know Brooklyn better than me."

"There's a really good diner a few blocks up. We should go there," Blair responded. It was one of her favorite places to go. She, Chuck and Serena went there at least twice a week. It was sort of their spot, and it was the perfect place to take Nate.

When they arrived at the restaurant, they sat across from each other in Blair's usual booth. It was obvious that everyone in the restaurant recognized who Blair was with, but Blair was determined to act natural. A waitress came immediately to hand them their menus.

"Here you are, Blair," the waitress said as she handed the menu to her.

"Thanks, Rita," Blair smiled sweetly before looking back up at Nate.

"I still can't believe you're here!" Blair said shaking her head.

"It was just something I had to do," Nate said nonchalantly.

"Sure, flying all the way across the country to go to a diner in Brooklyn," Blair laughed at the ridiculousness of the situation.

"I just couldn't let the other night be the last time I ever saw you," he said seriously.

"Can I just stop you right there and remind you of one thing?" Blair asked him.

"What's that?"

"I'm nobody," she said matter-of-factly. And it was true, she was just Blair Waldorf from Brooklyn that worked at a coffee shop and still lived at home with her father. She just couldn't bring herself to understand why a guy like Nate Archibald wanted anything to do with her.

"Blair, nobody is nobody. Look, I'm just following my gut. Sometimes you have to do that, even if what you are doing seems crazy," he responded. He didn't know why but after their dinner the other night, he couldn't stop thinking about Blair and he just knew he needed to see her again.

"Because," he continued, noticing that Blair still wasn't convinced, "in the gap between what prudence says we should do and what our heart tells us we must do, well, Blair therein lies our humanity."

"That's from _The Road to El Dorado_." Blair commented, immediately recognizing the line from his movie.

Nate laughed nervously. "You really are a big fan aren't you?"

Blair nodded laughing, before she realized what this meant. "Is that how you get women? Using lines from your own movies?" she asked shocked at the notion.

"Not anymore," Nate mumbled under his breath as he reached for his menu.

"I hope not because that would seriously shoot a hole in your credibility."

"No, look the truth is, that when we went on our date, you said something that really resonated with me. You said you were sure I had my priorities straight. Here's the thing, I don't. I really don't. My entire life since I was a teenager has been about becoming famous, becoming successful, becoming this…thing that I am and you were right, it really is unsatisfying. I need a positive influence, I need someone with solid and substantial qualities, someone who seems to understand life and how to live it in a good and happy way, like you. I just want to be around you. I want some of that goodness to rub off on me."

Blair smiled at Nate throughout his heartfelt speech, but couldn't help but be confused. "Do you mean goodness in a romantic way?"

"No, no, platonic goodness," he assured her. "And I mean that very seriously, no funny business here," he continued. He wanted to assure her that this wasn't just some excuse to get into her pants. He really did want help setting his life on track.

Blair's face fell a little, disappointed.

"Did I say something wrong?" Nate asked as he saw the expression on her face.

"No, no, I think it's great what you're trying to do," Blair replied as convincingly as possible. "So, are you going to be in Brooklyn for a while then?"

"I think I have to be. If I'm going to reset my priorities, I gotta get out of L.A., I gotta get out of that fishbowl," he explained as he turned to look out the window. Outside there were almost twenty people staring in at the fact that Nate Archibald was in their local diner.

Nate waved at the people and turned back to Blair chuckling awkwardly.

"So, what do you say?" Nate asked.

"I say…yikesabee!" Blair said and went back to her menu.

Nate sat confused for a few seconds before asking, "What does that mean?"

"Oh, it's just something my dad and I say sometimes when life surprises you in a way like this and there's nowhere to go but forward," Blair explained easily.

Nate was still confused. "So is that like, yes?"

Blair laughed, "Yes."

"Yes," Nate agreed.

***

After lunch, Nate dropped her off back at the café.

"So I'll see you at seven, then?" he asked as she got out of the car.

"Yes, see you at seven," she smiled as she shut the door of the car.

"Okay, then," Nate smiled as he drove off.

Blair smiled looking after him before turning quickly to tell her friends everything. She walked into the café and was immediately embarrassed to see that everyone in the café was applauding her. They had obviously all witnessed her getting out of Nate Archibald's car. She curtsied awkwardly before rushing over to where Serena was jumping up and down giddily and Chuck was standing watching the scene without amusement. Blair walked back to Chuck's office to get her things. Chuck watched her go and shook his head looking down. This was not going to be good.

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**So what do you think? I know there isn't a lot of CB interaction in this one, but bear with me! Please please review and tell me what you think!**

**Also, can I just say one quick thing about this week's Gossip Girl. ABSOLUTELY AMAZING. Ed & Leighton were so good! Especially Ed! I cried! Ahhhhh so good. Okay, anyways..review!**


	8. Chapter Eight

**A/N: Thanks so much for all the reviews/favorites/alerts! Here's the next chapter! Hope you like it!**

**I do not own Gossip Girl or Win A Date with Tad Hamilton!**

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**Win A Date With Nate Archibald!**

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Chapter Eight

At around five o'clock that night, Chuck, Blair, and Serena were getting ready to finish closing up for the night. On Tuesdays, Jammin Java always closed early, mostly to give Chuck and the girls a night off from work each week. Chuck was closing up the register while Blair and Serena finished cleaning off tables.

"So where are you guys going on your date?" Serena asked excitedly as she placed chairs on top of the tables.

"It's not a date, S! And I'm thinking of taking him to go see a movie," Blair replied as she grabbed two beers from behind the bar and sat at a table offering one to Serena.

"Oh, B, it is so a date! Dinner and a movie, come on, that's like textbook date," Serena stated as she sat down next to Blair.

"S, I'm telling you, it isn't a date. It's just two friends hanging out."

"Right, like Nate Archibald flew all this way just to 'hang out'", Chuck scoffed as he sat down across from the girls with a beer and a plate of nachos in hand. The situation he found himself in was getting worse every second. What should have been a onetime fairy tale date now seemed to be quickly turning into a full on relationship and the thought of it made his stomach turn.

"You guys, I'm serious. Today at lunch we had a really serious talk about his life and his priorities. He told me that he wanted help getting his life back on track. He said I had a lot of good in me and he wants that to rub off on him," Blair explained as she dug into the plate of nachos that Chuck had brought over.

"Wait, he wants your goodness to rub off on him?" Chuck asked trying to clarify what Nate had told her.

"I know right?" Blair said giggling, clearly satisfied with herself.

"Oh my gosh, B, that is so sweet," Serena sighed.

"And you actually believe this," Chuck said surprisingly, even though it came out as more of a question.

"Yeah, why wouldn't I?"

"Wow, Blair, wow…there's innocent, there's childlike, and then there's just asking for it," Chuck started.

"Chuck, come on…"

"Look, he wants your goodness to rub off on him? Please, he wants your ass to rub off on him is more like it."

"Chuck you are so wrong," Blair defended. "Nate isn't like that. He's not here for that. Trust me."

"Look guys, as much as I'd like to stay and listen to you argue about Nate's intentions, I have yoga class to get to. B, I'll call you later, and Chuck stop harassing her!" Serena said as she got up and left the café.

"Well, I better go too, I have to go home and get ready," Blair said.

"Wait, Blair listen to me—" Chuck tried to argue.

"No, Chuck, you listen. Nate isn't like that, okay? He just wants to be friends. And anyways, he would never be interested in me that way."

"How can you think that?" Chuck asked astounded at the fact that she had no idea how beautiful she was.

"Please, he dates beautiful Hollywood models and actresses. I can't even compare to them."

Chuck looked at her dumbstruck. She could be so stupid sometimes it made him so angry. "Blair, you are so amazing. You're smart, funny, beautiful, Archibald would be lucky to have someone like you."

"Chuck, you're just saying that because you're my best friend and you have to say that. It's sweet of you to say, really."

"God, Blair, I'm not just saying that!" Chuck said, extremely frustrated. "You have no idea how fucking gorgeous you are."

Blair sat shocked, not really knowing how to respond. Chuck had just called her beautiful and gorgeous, and it made her insides dance. She didn't know where it was coming from, but it scared her a little.

"Look, I'm just saying be careful, okay? Unless the man is gay…which actually could be a possibility…" he joked, "he's into you. Just trust me." He stood up from the table grabbing the empty beer bottles and disappeared into the kitchen, leaving Blair to think about what he had said.

***

Nate was getting ready in his hotel room when his cell phone rang. He looked at the caller ID and saw that it was Richard. He groaned before picking up the phone.

"Hello."

"_Hi, big guy!"_ Richard exclaimed into the phone.

"Hey man," Nate responded, trying to sound as enthusiastic as Richard was to talk to him.

"_Where the hell are you?"_ Richard asked from his office in L.A.

"I'm in Brooklyn," Nate responded as he went to his suitcase to find something to wear.

"_Okay…words I never thought I'd ever hear you utter,"_ Richard sighed sitting in his desk chair.

"Well, I'm visiting someone here, so,"

"_Who?"_

"The girl from the charity thing," Nate explained as he picked out a shirt.

"_The 'Win a Date' girl?"_ Richard asked confused. _"You flew all the way to Brooklyn and are staying in some motel in order to nail the 'Win a Date' girl?"_

"Woah, woah, I don't want to _nail_ her. Please don't put it in those terms."

"_Oh, forgive me Lord Byron,"_ Richard mocked sarcastically using a fake British accent.

"I just want to be around her, you know? She has a goodness. There's a lot I can learn from her. I'm trying to feed my soul, okay? I'm trying to find a way to actually be happy."

"_Oh so you want to be happy now?"_

"Look, this is big for me Richard."

"_Oh, God,"_ Richard sighed, worried about the mental health of his client.

"This is a turning point for me," Nate continued, trying to explain to his agent what he needed to do.

"_You think that today, Nate. But by the end of the week, when you've nailed her, you're going to feel differently. And what do you suppose happens then, huh?" _

"I don't— "

"_I'll tell you what happens then. You pulverize her heart, and then the press finds out, and all the good that was done by the 'Win a Date' promotion gets washed away, just like that. And, Jimmy Ing continues breathing. People like you cannot have relationships with girls from the Bronx."_

"It's Brooklyn," Nate said annoyed.

"_Whatever it is!"_ Richard claimed.

"Why not?"

"_Because, you're too different! You're values are different. For example, she has them."_

"No, this can work," Nate tried to convince Richard, as well as himself.

"_It can't! And when it ends, it's very bad for business."_

"There are more important things than business for god sakes," Nate argued.

Richard sighed. _"I don't even know who I'm talking to now. Hello? Is this Nate? What have you done with Nate?"_

Nate rolled his eyes and sighed. "Look, I got to go okay?" Looking at his clock, it was almost time to pick Blair up for their date.

"_No, you do not got to go. You're going through some kind of phase, right now. Some kind of extreme version of your normal in-between-jobs insanity. And it has a hold of you. You need to come back to L.A., have a Percocet, go out on a date with an actress looking to advance her career and end this self-destructive behavior!"_

"I'll talk to you soon," Nate said finally deciding to just hang up on Richard.

"_No, Nate. Bad, Nate."_

"Bye Richard."

"_Don't hang up on me!"_

Nate groaned when he finally hung up the phone. God, what a pain Richard can be. Nate took a deep breath and went back to getting ready for his date with Blair, trying to forget the horrific conversation he just had with his agent.

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**What do you guys think? I've been getting some people saying they don't like hearing about Nate's side of things, what do you guys think? I might stop if enough people ask me to! REVIEW PLEASEEEEEEEEEEEEEEEE! :)**


	9. Chapter Nine

**Happy New Year everyone! Enjoy!**

**I do not own Gossip Girl or Win A Date With Tad Hamilton.**

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Win A Date With Nate Archibald!

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Chapter Nine

At 6:45, Nate left the motel he was staying in and headed over to pick up Blair from her house. He knew she still lived with her father, and he was slightly nervous about having to meet the man. The date itself didn't make him any less nervous either. He wasn't sure how Blair felt about their outing tonight, and he hoped she might feel the same way he did and try a relationship. Yes, he had told her that he just wanted to be friends, but he was lying to himself if he said he didn't want more.

He arrived promptly at 7:00 and knocked on Blair's front door waiting anxiously to see her. He wore jeans and a button up long-sleeved shirt and hoped he wasn't over or underdressed. He was finally greeted at the door by a man that must have been Blair's father.

"Hi, you must be Nate," the man said before smiling. "Must be…you are Nate, I know who you are," he laughed as he ushered the movie star into his house.

"Nice to meet you Mr. Waldorf," Nate said extending his hand.

"Oh it's Harold for god sakes, please come and have a seat. Blair should be down in a minute."

"Thanks," Nate said as he took a seat on the couch and tried to make himself comfortable.

Harold walked into the kitchen and called back out to Nate. "Can I offer you a chocolate martini?"

"Oh wow, look at that," Nate commented.

"I hear they're pretty big out your way," Harold said trying to impress the house guest.

"Um, yeah…I guess they are," Nate agreed with the man. "But um, I'm driving, so...no thank you."

"Good answer," Harold smiled as he poured himself a glass and joined Nate back in the living room.

"So I hear your last movie just about topped 100 million, that's fantastic," Harold said as he sipped on the martini.

"Oh, uh, I guess it did yeah. Thanks," Nate replied unsure what to say. He didn't really keep up with the earnings of his movies and he felt a little awkward discussing it.

Just then, Blair came down the stairs and into the living room wearing a casual skirt and shirt with a cardigan over top. Nate thought she looked gorgeous and immediately stood up from the couch to greet her.

"Hey," he said walking up to her.

"Hi!" she responded sweetly. "I see you've met dad."

"Yeah, we were just talking shop," Nate commented.

Harold smiled and nodded.

Blair turned back to Nate. "So what did you want to do tonight? I was thinking we could go see a movie or something."

"Yeah, sure, a movie sounds great."

"Oh, have you seen _King Arthur of Britain_ yet?" Blair asked.

"I've been wanting to," Nate replied, trying to rack his brain to figure out if he knew what she was talking about.

"Well, have a great time guys. Have her back by dawn, and uh, no cocaine," Harold said standing up to Nate.

"No sir," Nate replied and laughed a bit at what he hoped was a joke.

Blair rolled her eyes, embarrassed by her father's behavior. Nate turned to leave toward the front door and as Blair went to follow Harold stopped her.

"How was I?" he asked in hushed tones.

Blair laughed and smiled. "You were great daddy."

"Okay, good. Have a great time sweetie," he said as he kissed her forehead.

***

After arriving at the movie theater and ordering them each a bag of popcorn and a soda, they made their way to their specific theater. As they walked through they ran into a cardboard cutout of Nate from his most recent movie. Nate paused and pointed at it smiling back at Blair.

"You look so sad there," she commented.

"Well give me a break, I just lost my wife and my goat," he joked.

Blair laughed and turned to keep walking, Nate following close behind.

***

Back at his apartment, Chuck sat in front of his TV with some food as he tried to forget the fact that Blair was currently on a date with Nate Archibald. He flipped through the channels landing on a war movie that starred Nate Archibald. Sighing he changed the channel again only to land on an old interview of Nate Archibald. Rolling his eyes again, he changed the channel, and this time a Spanish soda commercial starring Nate Archibald hit the screen. Chuck scoffed and shut the TV off, his attempts of blocking Nate and Blair out of his head failing miserably.

He got up off the couch tossing the remote off to the side and went back into the kitchen to find something else to occupy his time.

***

After the movie had finished, Blair and Nate casually strolled out of the movie theater side by side. Blair kept looking over at Nate and couldn't help but smile. _Okay so maybe this could be a date,_ she thought to herself.

"So what do people usually do at this point in the evening here in Brooklyn?" Nate asked.

"Well, they go to the diner," Blair suggested.

"We could do that, I mean we haven't eaten anything in…fifteen minutes?" Nate joked looking at his watch.

Blair laughed. "Or they go home."

"It is a school night," Nate said jokingly.

"Of course if this were a date," Blair began, "we might go to the Heights Promenade."

"And what do people do there?" he asked.

"They park," Blair said nervously.

"And then?" Nate asked stepping a bit closer to Blair.

"And then…they marvel at the what a magnificent sight the Brooklyn skyline is," Blair explained almost sarcastically.

"But this isn't a date, so we can't do that," Nate said matter-of-factly.

"Right, no, of course," Blair said trying her best to hide her disappointment. It didn't work.

"Blair, look, I don't want to do anything to harm the friendship," he explained reaching out to touch her arm.

"Oh, no, me neither," Blair agreed.

Fifteen minutes later, Blair found herself parked in a convertible at the Heights, making out with Nate Archibald. She didn't know how she got her, but she sure wasn't complaining. Her cardigan was off and tossed to the side, and Nate's shirt was unbuttoned almost halfway down his chest. She couldn't believe that she was here, with Nate Archibald.

Just then, his phone started to ring. Nate groaned as Blair pulled away. Nate reached into his pocket to take out his phone. Looking at the caller ID, he saw that it was Richard calling, and he had no desire to be talking to Richard at that precise moment. Not thinking, he turned off the phone and chucked it out of the car over the cliff.

Blair looked over at him in shock, and Nate just smiled pulling her back in to kiss him. Blair giggled and moved her way back closer to him in the car.

***

Harold sat at home reading a book and drinking coffee as the phone rang.

"Hello?"

"Hi, Mr. Waldorf, it's Chuck."

"Oh, hiya Chuck. Uh, Blair's not here. She's out with Nate Archibald," he responded into the phone.

"Oh uh really? I hadn't… uh, okay, cool. Good for her then," Chuck said trying to play off the fact that Blair's date was the only thing he could think about the entire afternoon and evening.

"You know Chuck, he seems like a very nice guy," Harold said somewhat catching on to Chuck's concern.

"He does, a lovely…lovely guy. So um, where did they go?" Chuck asked casually.

"I think they went to see a movie," Harold responded.

"Oh, great a movie, so I guess the 7:00 would get out at like 8:45, 8:50," Chuck started looking at his watch before pausing to realize how stalkerish that sounded, "or so someone happened to uh mention to me in passing. Uh, so I guess that would put them out and about and onto their next…activity."

"I guess it would Chuck." Harold could tell that the date was worrying Chuck and he felt for the kid. "Look, I'll leave Blair a note that you called."

"Oh yeah, uh I just had an inventory question…uh, about the café, but uh, no don't worry about it, we can just clear that up tomorrow," Chuck said pulling shit straight from his ass.

"Okay, Chuck, goodnight," Harold laughed.

"All right," Chuck replied before hanging up the phone and rubbing his hands over his face. _Well that wasn't obvious_, Chuck thought silently cursing himself for seeming so pathetic.

***

Back in the car, Nate pulled back from their make out session. "Blair?" he whispered. He wanted to know what she was feeling and if she was okay with what was happening.

"Yeah?" she asked, slightly breathlessly.

Before Nate could finish his thought, they both jumped back when they heard a police siren. They looked over the side of the car and saw two cops walking up to them.

"Hi, could I see your driver's license and registra—" the cop started before realizing that Nate Archibald was in the driver's seat of the car. "Yikes-a-bee. Blair?" The cop finally realized that his old high school classmate was in the car with him.

"Hi, Tom," Blair smiled awkwardly. She felt extremely uncomfortable being caught in this situation.

"Hi, wow," Tom laughed nervously. "Oh boy."

Blair felt more and more uncomfortable noticing that Tom was clearly recognizing the position he had just caught them in. "Ok, then…"

"We uh, we heard you were in town, Mr. Archibald," Tom stated, a little star struck.

"Did you?" Nate replied feeling just as awkward as Blair was.

"Pretty fond of our Blair, over there, huh?" Tom tried to joke.

"Uh, yes, yes I am, Officer," Nate agreed not believing this was a conversation he was having with a cop.

Blair laughed nervously. "Uh, Tom…?" she asked wondering if he was ever going to get to the point.

"Right, right, uh, listen, we got a call saying that someone was parked here, and you know it's illegal after sunset, so…"

"You got a call at this hour?" Blair asked confused.

"Yeah."

"From who, a squirrel?"

Before Tom could answer, Blair heard the sounds of a car tires screeching and looked back over her shoulder. The car was driving away, but she caught the tail end and recognized the car immediately.

"Never mind," she sighed.

Tom agreed to let them off with a warning and Nate drove her home.

"I am going to kill that Chuck, bring him back to life, and kill him again!" Blair exclaimed frustrated that Chuck would do such a thing and ruin her date.

Nate got out of the car, opening Blair's door for her as he listened to her vent. "Look, just calm down, calm down."

"Well why aren't you upset?" she asked as they made their way to her front door.

"Because it doesn't matter. OK? What happened here tonight was a force of nature. Two people set out to be friends…but nature would have none of it. Nature wanted them to be more. And nature is going to want that tomorrow," Nate smiled; satisfied with the little speech he just gave.

Blair smiled before giving him a kiss goodnight, and turning back into her house.

***

The next morning, Blair sat at an open table refilling sugar containers.

"What did I tell you?" Chuck asked as he came up behind her, startling her a little. "What did I tell you about your carnal treasure?"

Blair sighed and decided to play along. "You said to guard it."

"I said to guard it. And what did you do? You practically chucked it at him," Chuck spat in an annoyed tone.

"Chuck, you're acting like it was some sleazy night. It wasn't. It was classy." Blair assured him, also trying to assure herself.

"Oh... classy_... right_. I mean it's not like he took you to the movies and felt you up in his car," Chuck mocked.

"The evening evolved, Chuck," Blair sighed exasperated.

Chuck was silent for a minute. "Oh my God, did he actually say that?"

"It started out as two friends going to the movies…" she began.

"And it evolved into dry humping," Chuck finished for her.

"He fought it! He didn't want to do anything that might wreck the friendship."

Chuck stood back and laughed at the ridiculousness of what she had just said. "Wow...did he actually... I can't believe he used that line. And…I can't believe that you bought it."

"It wasn't a line Chuck," Blair defended, putting down the sugar and looking up at him.

"Okay, um excuse me, guys," Chuck called the attention of a group of guys sitting at the bar drinking coffee, "a show of hands please. Who here has used some form of the 'don't want to harm the friendship' line," he asked them raising his own hand.

All four men raised their hands and Blair opened her mouth in shock. Chuck just smirked at being right. Serena who had been cleaning the table next to where Blair was sitting decided to come over and talk to Blair.

"Blair? What are Nate's pectorals like to the touch? Are they warm yet firm like…"

"S, that's _really_ not helping right now," Chuck cut her off.

"Sorry Chuck, got caught up," she said as she went back to cleaning, all while eavesdropping in on what Chuck was going to say next to the girl he was so obviously in love with.

"Listen, Blair," Chuck started as he sat in front of her. "Listen to me, bottom line. Nate Archibald is an actor, OK? How do you know that he's not acting with you?" Chuck asked in a serious and concerned tone.

"He's not acting." Blair responded immediately completely sure of her answer.

"No. He is. He's playing a role. The role of Hollywood bad boy trying to find virtue," Chuck said calmly, trying his best to say what he needed to say without hurting her feelings.

"Chuck, he's not," Blair insisted.

"Look…after he…gets what he wants from you a couple of times…he is out of here, OK? You will never see him again."

Blair shook her head not believing what Chuck was saying to her. "And you would know exactly what that's like right Chuck? Mr. I sleep with girls all the time and never call them back. Look Chuck, maybe that's how you handle things, but Nate isn't like that. I know it."

Chuck sat back in the chair, shocked at what Blair had just said to him. He couldn't believe that that was how Blair saw him, and he was extremely hurt by the statement. "Well, I hope you're right then."

Blair watched a clearly hurt Chuck get up from the chair across from her and make his way towards his office. She felt bad about what she had said. Yes, Chuck was a bit of a player, but she may have exaggerated it a bit. She just couldn't believe that Chuck would insinuate that Nate was just using her for sex and then that was it. She refused to believe it was true, not after the things Nate had said to her.

Nate burst into the café, breaking her out of her reverie. "Blair, guess what? I bought a house. I bought a house! Can you believe it?" he exclaimed waving around what appeared to be the contract in his hands.

Chuck, who had not quite reached his office, heard everything and turned to look at the scene before him. Nate sat in the chair that he had moments ago been sitting in and pulled Blair into a hug.

"Really, you bought a house?" Blair asked completely taken aback by the situation.

"I bought a house," he confirmed with a huge smile on his face. "It needs a little work, but I bought a house."

"Wow, you bought a house," Blair repeated as she turned to look back at Chuck, giving him an 'I told you so' look.

"We're putting down roots, baby," Nate said as he leaned in to kiss her cheek.

Blair squealed giddily and hugged Nate again. Serena was also squealing until she turned and saw the look on Chuck's face as he watched them. It was a look of sadness…and maybe even heartbreak? Serena knew that Chuck was crazy about Blair, but he never acted on it. It's his fault that he waited so long, and now someone else was swooping in and sweeping Blair off of her feet, and she couldn't be happier for her.

"You have to come see it, maybe after work?" Nate asked excitedly.

"I'd love to!" Blair replied happily.

"Yeah, I'd love to," Chuck repeated as he moved closer to the happy couple. "Congrats, man, a house."

Blair and Nate looked at each other confused before turning to look at Chuck. Nate had obviously wanted it to just be him and Blair, but he figured if he was sticking around, he needed to get to know her friends.

"Great," Nate smiled. "I'd love for you to come see it. You too, Serena."

"Great!" Serena exclaimed.

"Great." Chuck agreed.

"Great," Blair sighed. _This will be interesting_, Blair thought.

* * *

**Okay so what does everyone think? For those of you that have seen the movie, I am trying to keep it pretty close to the events in the movie with my own twist, so for those who haven't seen it, the story might seem a bit weird or slow. But stick with me!**

**Anyways, reviews are greatly appreciated and loved :)**


	10. Chapter Ten

**I am sooo so sorry about how long this update took, school has been kicking my butt and I've started a new fic called My Love Will Follow You, please check it out! Anyways this story is coming to an end soon, probably three or four more chapters. Thank you so much for all of the reviews and sticking with me!**

**I do not own Gossip Girl or Win A Date With Tad Hamilton.**

* * *

Win A Date With Nate Archibald

* * *

Chapter Ten

After work, Blair and Serena hopped into Chuck's car in preparation for their trip to Nate's new house.

Blair couldn't be more excited. Nate was really getting serious about sticking around and trying to make things work and she was so happy with everything that was happening between them.

"So he's going to keep staying at the motel while he fixes up the place," Blair explained as they drove.

"Like, he's a carpenter all of the sudden?" Chuck asked sarcastically.

"I'm sure he'll do a great job on the house," Blair responded truthfully.

"Blair, he's from Malibu, California. The only things they build there are tanning salons," retorted.

"Could you like, smile for a second?" Blair sighed.

"This changes nothing," Chuck stated matter-of-factly.

"Ugh, you are unbelievable," Blair said rolling her eyes.

"Blair, people like this buy houses all the time—it's called a tax shelter."

"Ugh, Chuck!"

"Listen, I guarantee you that by the end of today, Nate's house will be right back on the market."

"Why, what are you going to do?" Blair asked suspiciously.

"Nothing. You know—just be a good neighbor," Chuck replied innocently. In reality, Chuck did have a plan. A plan to get Nate out once and for all. He was going to show Nate how hard it was to fix a house and keep it in shape and hopefully convince him that buying the house was a huge mistake.

The three friends pulled up the driveway of Nate's new house to find Nate standing on the front porch to greet them. It was a gorgeous house. Two stories with a beautiful wraparound porch. And the plot of land it was on was beyond huge. It was big enough to maybe have a barn and some stables. Blair was in awe of how big and beautiful it was.

"Nate, this place is amazing!" Blair exclaimed as she got out of the car and ran to Nate to give him a quick peck on the lips.

"Thanks, I really like it," Nate replied, sliding his arm around Blair's waist.

Nate led them inside the house and out through the back door for everyone to see the enormous backyard.

"Now, this house sits on what they call the South-40. So, I'm not sure how many acres that is, but I'm sure it's a lot," Nate began the tour of his new purchase.

Chuck looked at Nate like he was the biggest idiot in the world before responding. "I'm gonna guess 40.

Nate looked around at the land. "Oh yeah, could be."

"Listen, Nate, I know that this place needs some fixing up and I'd be happy to lend you a few pointers on different chores around the house."

"Really? Chuck, yeah, that'd be great," Nate said as he patted Chuck's shoulder.

The four of them made their way into the house where Nate led them to the kitchen.

"So the plumbing in the sink has been acting up, I was going to try and fix that first," Nate told Chuck.

"Okay, well this can be a bit complicated. Your gonna want to go under the sink and carefully unscrew the pipe to make sure there's nothing clogged in there. But be careful not to spill everything everywhere, and you want to watch that you don't crack the pipe to prevent leakage," Chuck described. "If you want, I can do it for you."

"No, man I want to try this myself, thanks though."

The three friends watched as Nate unscrewed the pipe with ease, cleared out any possible blockage, put the pipes back together and turn the water faucet on, all in a matter of minutes. The water flowed out perfectly. Blair and Serena were beyond impressed. A man that could fix a broken pipe was a good man to have around.

"Wow, where'd you learn to do that?" Chuck asked dumbfounded that he had such an easy time fixing the pipe.

"Chuck, do you remember my movie 'Joe Plumber'?"

"Of course," Chuck sighed. His plan wasn't working very well so far.

Next, the group made their way to the entertainment room where Nate was looking to install a television.

"Okay so here you want to get the mounts in the wall first, before hanging the TV up on there. But be aware of the studs in the wall otherwise the mounts won't stay up. And make sure you make them sturdy, you don't want your fancy plasma TV falling to the ground," Chuck explained.

Nate immediately went to work nailing the mounts into the wall. He finished securing them and after Chuck gave his approval that they were indeed perfectly put into the wall, Nate went to lift the TV.

"Here let me help you with that," Chuck offered making his way over to the TV as well.

The two men lifted the TV, only to have Chuck drop his side almost immediately.

"Wow that thing is heavy," Chuck tried laughing it off.

Blair and Serena gave each other strange looks.

"You know what man? I got it," Nate said as he wrapped both his arms around the front of the TV and lifted it onto the mounts.

Serena and Blair gushed over Nate's muscular strength and Chuck just sighed.

"Well, it seems the luck continues, that's great man," Chuck said.

"Chuck, did you ever see my remake of 'The Cable Guy'?" Nate asked.

"If it came out, Nate," Chuck said as he looked over at his two best friends, "then I saw it."

***

That night after (much to Chuck's chagrin) Nate got all of his chores done, the four of them decided to hang out at Jammin' Java.

Nate, Blair and Serena sat at a table with a bunch of other people as they listened to Nate tell stories of his days on set on his many movies. Everyone, including Blair, was extremely impressed with all of the things that Nate had experienced.

Chuck, meanwhile, was taking out his frustration on a game of darts. His plan to make Nate look bad and to convince him to not buy his house had failed. The day had actually made Blair seem to fall even more under Nate's spell and it made Chuck physically sick. He was realizing how fast his chances with Blair were disappearing and it made him extremely uneasy.

After throwing some pretty terrible darts, Chuck barely noticed that he had hit a bull's-eye—something he and Blair had been competing over for a long time. He couldn't believe it.

"Oh my God, Blair! Blair, come look at this," Chuck yelled as he turned his attention over to where they were sitting. What he saw made his heart drop. Blair and Nate were engrossed in a full-on make out session, completely oblivious to everyone surrounding them. Chuck eventually looked away; his heart couldn't really take watching the love of his life kissing some other guy. He looked down at the ground and shook his head before turning and making his way to the bathrooms.

In the bathroom, Chuck splashed cold water over his face in an effort to try and relax. It wasn't really working. As he dried his face off he noticed Nate enter the bathroom and make his way into a stall. He knew this probably wasn't the best time for this, but there were some things he needed to say to Nate.

He stalked over to the stall Nate had just entered and kicked it open.

"Woah, Chuck!" Nate said as he reached down to cover his man-business. His pants were at his ankles as he sat on the toilet seat.

"Hey Nate. Can I talk to you for a sec?" Chuck asked firmly.

"Uh, yeah, sure," Nate replied even though he found the situation they were in extremely awkward.

"Forgive the intrusion, but I uh—" Chuck began.

"No, uh, please. Fire away," Nate sighed.

"Okay, here it goes," Chuck said as he shifted his feet and cleared his throat. "You win, okay? Fair and square. You win."

"Thank you," Nate responded.

"I mean you did have an advantage or two…but uh, the bottom line is that I want Blair to be happy, so I just had a couple questions. Do you know how long she keeps her hair in straight mode and how long in curly?"

"Uh..what?"

"Or why her favorite necklace is a butterfly-shaped clasp?"

"Uh, no."

"Did you know that she has six different smiles?" Chuck continued.

"Uh, she has six smiles…?" Nate didn't really know how to respond to all of this. He had only known Blair a few days, and Chuck had known her all of his life.

"Yeah, one when something just flat-out makes her laugh, and one where she's just laughing out of politeness. But there's one when she makes plans, mostly scheming ones. One when she makes fun of herself. One when she's uncomfortable, and one…one when she's talking about her friends."

"Uh, I uh, I don't know any of that Chuck," Nate said calmly.

"No you don't Nate. She's more of a…a treasure, then you could _possibly_ know. She's not just some wholesome, small town girl from Brooklyn, some like good for you, breath of fresh air. Nate, she is an amazing person, with a huge heart, and the kind of beauty…that a guy only sees once, you know, once."

Nate just shifted uncomfortably. It was so obvious that Chuck was in love with her and he certainly felt weird about taking that away from him—but he really liked Blair, and he wasn't going to give that up.

"Look, Nate, I know she likes you—a lot. But I also know how easy it would be for you to break her heart, so please, if there's any chance that will happen, just walk away. For her sake."

"Chuck, I could never break Blair's heart. Okay?" Nate assured her best friend.

"Good. Because if you do I swear to God I will tear you to pieces with my bear hands," Chuck threatened.

Nate smiled at Chuck's loyalty. "You're a good guy, Chuck."

Chuck sighed and looked to the ground. "Yeah well, apparently not good enough."

Nate looked around a bit before reaching out and cutting himself a large sheet of toiled paper and looked back up at Chuck.

"Right well, finish up here, but just…take care of her, Nate." Chuck said before leaving the stall.

***

Later that night, Blair found herself in a motel room, on a bed, making out with Nate Archibald. She didn't understand how she got here, but she wasn't complaining.

"You're a good kisser," she commented in between kisses. "But I guess that doesn't come as a surprise for you to hear."

Nate laughed. "No, not really. You're a really good kisser too."

"Oh really? Even compared to Hollywood girls?" Blair asked.

"Yeah," Nate confirmed honestly.

Blair laughed. "Well that's just ridiculous."

"It's not," Nate responded as he leaned down to kiss her again. Blair responded eagerly until she felt Nate's hands beginning to unbutton her blouse. She immediately reached her hand down to cover his and just as she was about to stop him, there was a knock at his door. _Saved by the bell_, Blair thought.

"Oh Nate!" a voice called from outside.

"You're favorite two people are here," called another.

"Oh you've got to be kidding me," Nate said as he sat up on the bed.

"Who is it?" Blair asked.

"It's my agent and my manager," Nate sighed as the knocking continued.

"Oh Nathaaannnielll," he heard Richard call.

"This isn't happening," Nate said as he got up off the bed to open the door.

Before he did, he turned back to Blair. "I'd like to apologize in advance for these two."

Blair laughed nervously as she scooted to the edge of the bed and made sure that her blouse was back to being buttoned perfectly.

Nate finally opened the door to find his agent and his manager smiling widely at him.

"Nateee," Richard drawled out.

"Nathaniel Archibald," Levy greeted before pushing past him to get into the room.

Nate followed the two men back into the room and turned to Blair.

"Uh, this is my agent Richard Levy and my manager, Richard Levy."

"Uh, you're both named Richard Levy?" she asked confused.

"Who isn't?" Richard responded happily.

"You. You must be Blair," Levy said as he made his way over to where she was standing.

"Uh, yes, nice to meet you," Blair said sweetly.

"Did we come at a bad time?" Richard asked, somewhat sincerely.

"I hope so," Levy joked.

"Actually, yes," Nate said annoyed.

"Well, Nate, Jimmy Ing stopped breathing," Richard informed his client happily.

"What?" Nate asked excitedly.

"You got the part, pal!" Levy exclaimed.

"It seems that he saw something that reminded him that he had to have you," Richard explained.

"It was the body of your work—" Levy began.

"I knew it!" Nate exclaimed.

"Your credits," Levy continued. "The reality of you, and who you are."

Nate smiled widely and looked over at Richard for reassurance. Levy tended to exaggerate quite a bit.

"Exactly! He finally realized that Nate Archibald _has_ to play this part."

"Has to," Nate repeated in agreement.

"There's nobody else," Richard explained.

"Yes!" Nate exclaimed. "Oh my god this is so great."

Blair watched the entire scene play out in front of her and couldn't help but feel uneasy. This probably meant that Nate was leaving. Chuck was right, Nate was leaving.

"Oh fellas, I gotta tell you, I have never felt happier than I do in this moment, right now," Nate said.

Nate continued celebrating with his agent and his manager before turning to Blair and giving her a huge hug and kiss on the cheek.

"So then you're leaving," Blair commented.

"Yes," Nate said happily.

"Yup, you've got fittings all day Monday and rehearsals start Tuesday," Richard explained.

Blair's heart immediately dropped and she looked down to her lap at her folded hands.

Nate still couldn't contain his excitement.

"Wow, things happen fast, huh?" Blair said looking over at Nate.

Nate finally stopped celebrating and looked at Blair. He finally realized what this meant and immediately started thinking about the situation he was in. He didn't want to leave Blair, but he also was beyond ecstatic that he finally had a new part in a movie.

"Oh my god, you're right," Nate said to Blair.

"No, no, no, it's fine," Blair said as firmly as she could.

"I'm gonna turn it down," Nate said looking back at his managers.

"What?" Blair squealed, taken aback.

"What?"

"What?" both Richard and Levy repeated in shock.

"I talked about fixing my priorities and at the first opportunity, I'm abandoning that," Nate explained.

"Nate, come on, you're not going to turn down the part, we both know that," Blair said.

Richard and Levy both nodded in agreement with what Blair was saying. They couldn't risk Nate turning down the part of a lifetime.

"Give us a minute, will you guys?" Nate asked his agents.

"We will be in the lobby," Richard said as both men made their way towards the door.

Once they had left, Nate turned back to Blair.

"I want you to go with me," Nate finally said.

"What?" Blair asked, surprised at the sudden invitation.

"I'm not taking the part unless you go with me."

"Really?" Blair asked as she now felt slightly flattered.

"Yeah. Blair have you been listening to anything I've told you? I love you."

Blair gasped at his confession. This was all happening so fast, she wasn't sure how she could believe it was really true.

"How many times in your life have you said that?"

"Uh…not counting the movies?" Nate asked nervously.

"Not counting,"

"Uh…I've said it a few times," Nate responded honestly. "But… I never knew what it meant until I met you."

Blair still felt apprehensive. There was no way he loved her after only a few days. She knew she didn't love him. She liked him a lot and she was falling for him, but she didn't love him. So there was no way he could love her already.

"I can't go with you, Nate. Because you don't love me. You maybe want to love me, but I think what you love right now, is the idea of me. You can't love someone for what they stand for or what they seem to be. You have to love them for the details, the little things that are true of them and only them."

"But I do love you for your details, Blair."

"You don't."

"I do."

"You couldn't possibly. You don't know what they are."

Nate was panicking. He wasn't ready to lose Blair and he was trying to think of what to say to make her believe what he was saying. The kind of love that she described was definitely the way Chuck loved her, so he thought back to the conversation they had in the bathroom.

"You have six smiles," he blurted out.

"What?"

"Yeah," Nate smiled, realizing that this could work. "You have six smiles. Did you know that?"

Blair didn't know what to say so she just shook her head.

"One when something really makes you laugh. One when you're just laughing out of politeness. One when you're scheming. One when you're making fun of yourself. One when you're uncomfortable and one when you're talking about your friends."

Blair couldn't stop herself from grinning like an idiot. That was the sweetest thing anyone had ever said to her and she couldn't believe that Nate Archibald had noticed those things about her. Maybe he really did love her.

"I told you," Nate smiled back.

"That is so much better than any speech from any of your movies," Blair laughed.

Nate smiled back but felt slightly guilty. He had stolen it directly from Chuck, but he was desperate. He couldn't have Blair leave him.

"So, will you come with me?" Nate asked hopefully.

Blair looked into his eyes and couldn't help but see sincerity in them. He really wanted her with him, she couldn't believe it. Saying yes would be a huge risk, but when had she ever taken a risk in her life? Maybe it was finally time to take a leap of faith.

"Yes," she finally said.

"Yes?" Nate repeated.

"Yes, Nate I would love to come with you," she smiled as she leaned back to lay on the bed and Nate climbed on top of her.

"What are you thinking?" Nate asked.

"Nothing. I'm done thinking. If I'm making the biggest mistake of my life, I don't even want to know."

"Hey, you're not making a mistake," Nate assured her as he leaned down to kiss her.

Blair kissed him back pushing any doubts as far back in her mind as possible.

* * *

**reviews are loveeee**


	11. Chapter Eleven

**I'm on a role with finishing this story! I have one chapter left and maybe an epilogue, we'll see! Thank you for reading and for all the reviews! Enjoy!**

**I do not own Gossip Girl or Win A Date With Tad Hamilton!**

* * *

Win A Date With Nate Archibald

* * *

Chapter Eleven

That same night, Chuck was sitting at the bar at Jammin Java nursing a glass of scotch as Angelica was cleaning off the bar. There were only a few customers left and they all seemed to be finishing up. Angelica immediately noticed Chuck's sour mood and she had a pretty good guess as to what-or rather who- was causing it.

"You know, as a bartender, you do learn to kind of recognize those customers that need to talk," Angelica said as she stood in front of him.

"Well, I'm not a customer, am I?" Chuck replied coolly. "Give me like…six more of these will you?" he asked referring to his glass.

"No, but Chuck, I think you _really_ need to talk," she pressed.

"Fine," Chuck sighed before continuing, "I think that our dear friend Blair might be falling in love with Nate Archibald."

Angelica nodded. "Yeah…didn't have to be a bartender to see that one coming."

Chuck smirked and looked down. He didn't know why he was being so open with Angelica. Be it the scotch, or his seriously depressed mood, he couldn't get himself to shut up.

"Right, but the problem with that…is that I'm in love with Blair."

Angelica smiled and looked back up at Chuck. "You know, I always thought that maybe you were."

Chuck didn't say anything. He just picked up his glass of scotch and drained its contents.

"So how much do you love her?" Angelica asked, folding her arms onto the bar. "Is it love, is it big love, or is it great love?"

"Angelica, I haven't the slightest fucking clue what you're talking about."

"Well, love you get over in two months. Big love, two years. And great love…well great love changes your life," she explained.

Chuck stared back at Angelica as he processed her little philosophy. He knew immediately what type he felt for Blair, and upon realizing it, his heart sunk even more. He finally looked down at his empty glass, never answering her question.

Angelica caught on quickly. "Oh my God. It's great love." She immediately reached for the bottle of scotch and began filling up Chuck's glass.

"Isn't that just _great_," Chuck commented as he gulped down the serving she had just given him.

"Well, you gotta win her back!" Angleica protested.

"Ang, she was never mine to being with. And anyways, I've already tried everything to get her attention; she's too blinded by Archibald."

"Well what did she say when you told her you love her?"

"Okay so maybe not _everything_."

"What did she say when you kissed her?"

"Alright so there's two things I haven't tried," Chuck admitted.

"Well what have you tried?"

"For the entire twenty years that I have known her, I have made it almost painfully obvious the way I feel about her. I've never exactly been subtle about it. She just…doesn't notice or doesn't feel the same, I don't know."

"Alright, get up," Angelica demanded.

"What?" Chuck asked.

"Get your ass off the barstool."

Chuck looked at her in shock. He couldn't believe she was speaking to him this way.

"If you feel it, Chuck, and you don't do everything in your power to get it, then you are basically slapping life in the face, so get up!"

"Listen sweetheart, I don't know if you've been paying attention, but I don't really stand a chance here."

"As my father told me when I didn't think I would get the job at this bar, 'honey, your odds go up when you file an application'."

"He's Nate fucking Archibald, Angelica. There is absolutely no competition. The guy wins by default."

"You _are_ Nate Archibald," Angelica stated.

"I'm sorry, come again?"

"Don't you see Chuck, everyone is Nate Archibald to someone. Blair is Nate Archibald to you. And you are Nate Archibald to me," she explained, fading softly at the last part. She had made a fool of herself many times in front of Chuck, but she really did truly like him.

Chuck felt slightly at her admission. He knew she liked to throw herself at him, but he didn't really think it went beyond an innocent crush. He stood up and leaned over the bar to place a kiss on her cheek.

"Thanks, Angelica."

"So start acting like it," she demanded changing the subject.

Chuck nodded and got up off the bar and reached for his coat.

"You know something? You are a really good bartender. I should give you a raise," he joked as he took one last swig of his scotch and walked out of the bar.

***

After making her decision to leave with Nate, Blair went home to start packing. Nate was on a schedule and they would have to leave pretty much immediately so that he could settle back in and fully get ready to start filming. Blair was both excited and extremely nervous. She couldn't believe that she was going to L.A. with Nate Archibald, as his girlfriend, and she got to see him film a movie. But she was also nervous about leaving home so quickly. She'd be leaving Serena and Chuck behind and her father. It was all happening really fast, but this was the opportunity of a lifetime. And when she really thought about it, what was keeping her in Brooklyn? Yeah she was taking college courses, and she loved her job at Jammin Java, but it wasn't really a career.

She continued moving all over her room, looking for different things to pack, thinking about her upcoming trip, when she heard a knock at her bedroom door. She turned and saw that it was Chuck standing in her doorway.

"Hi," she smiled putting down the shirt she had been holding.

"Hey," he responded coolly, waiting to be officially invited in to her room.

"Come in, come in," she said when she noticed his apprehension.

Chuck walked across her room until he was standing directly in front of her. "So um, there's something I wanted to talk to you about."

"Me too!" Blair exclaimed happily.

"Really? Uh, yeah, you go first," he said, his nerves getting the best of him.

"No, no, you go first," Blair demanded.

"No, seriously. You go first."

"Okay," she took a breath before continuing. "Nate got a part in a really huge movie and he asked me to go to California with him for the shoot! We leave tomorrow afternoon!" She was practically jumping up and down with excitement as she finished.

Chuck felt like his heart had literally crushed into a million pieces. He absolutely could not believe this was happening to him. A week ago, everything was perfect. It was just him, Blair and Serena. Now his best friend and the girl he was in love with was about to run off with a movie star.

"Isn't that great?" Blair asked when Chuck wasn't responding.

Chuck looked to the ground and shook his head. "I probably should have gone first."

"Why? What were you going to say?" Blair asked curiously.

Chuck continued to stare at the ground and shaek his head. This whole thing was his fault really. He had waited too long. He had been in love with her since they were five and if he had told her sooner, maybe things would be different. But he didn't. He had chickened out time and time again, he put on this show of dating a bunch of different girls, when he should have been telling Blair every single day how much he loved her and would always love her. She was so happy right now; he couldn't do anything now to spoil that.

"It was nothing," he said looking back up at her, "just, you know, travel safely, okay? And just really enjoy the shoot." He was blabbering; he really had no idea what to say now.

But then he remembered what Angelica had said. He had to tell her how he felt, and he had to do it now, even if it completely backfired on him.

"Actually, no. I remember what I was going to say," he said as he stepped forward, pulled her towards him, and kissed her.

He kissed her with as much passion and as much determination as he could muster, and it felt amazing. He had waited so long to do this, and now that he finally had, he felt alive.

Blair was taken completely by surprise, but found herself kissing him back. So many emotions were going through her head right now; she didn't really know what to think.

Chuck pulled back slightly before placing one last gentle peck on her lips. He pulled back completely and looked into her extremely wide brown eyes.

"I love you, Blair. I've been in love with you for longer then I'd like to admit. And I know I've been a complete jackass this entire week, but it's because I've been fighting for you. I don't want to lose you to Nate Archibald, or anybody else for that matter. It's you Blair; it's always been you for me."

Blair was in complete shock. She was still trying to regain her focus after that kiss that he had given her. Now he was saying he was in love with her and she couldn't believe what was happening.

"Say something, Blair," Chuck demanded softly.

"Now? You kiss me now? You say this to me now, after eighteen years of being my friend, you do this now?" Blair's head was spinning.

"Yes…to all questions," he said quietly, not really liking where this conversation was heading. He could feel her already starting to pull away.

"Umm, I have to pack," she said as she stepped back and turned to her suitcase.

"So that's it? I tell you I'm in love with you, and you don't even give me any type of response…because you have to pack?"

"Well not only do I have to pack, but I also have like a load of whites in the dryer and my dad called some of my relatives and they're all expecting me…so, you know, it's all in the works," Blair blabbered on as tears started to well up in her eyes. She had no idea why she was responding this way, why she was crying.

"Blair, just wait for a second, just stop for two seconds and talk to me. Can you honestly tell me that after three days, you are in love with Nate Archibald? That you're ready to follow him across the country? Is that really what's in your heart? Can you honestly say you feel nothing for me?"

Blair eyes continued to well up. She was so overwhelmed at the moment she didn't know what she felt.

"I'm sorry…" she mumbled softly.

Chuck just stared into her eyes and realized that he was too late. She made her decision. He kissed her, told her how he felt; there was nothing more he could do to change her mind. As much as it killed him, he knew it was time to let go.

"Yeah, I'm sorry too," he said before turning and leaving her alone in her room.

She immediately felt a terrible pain in her gut watching him walk away, but decided to ignore it. She brushed the tears out of her eyes and went back to packing. Chuck was too late. Nate was her future now.

***

Chuck stormed out of Blair's room and out of her house and ran into her father sitting on the front porch.

"You okay, Chuck?" Harold asked, noticing the boy's disheveled appearance.

"Yes sir," Chuck said as he straightened his back and did his best to put on a fake look of indifference.

Harold nodded. "Listen, Chuck, obviously we've all been a little seduced by Nate Archibald's presence. No one more so than me," he admitted recalling the embarrassing chocolate martini incident. "But that doesn't mean that I don't know at the end of the day who cares about my daughter most and who she would be with if the world were fair."

Chuck sighed and took a seat next to the man who had been more of a father figure to him than his own father was. Harold could see right through him.

"Well, it's not," Chuck said bitterly.

"No, no it's not," Harold agreed. "You're a good kid Chuck; you've got so much potential. Blair told me about your expansion offer, and I think you need to take it. You don't get many opportunities like that in a lifetime."

"Thanks Mr. Waldorf, I think I will," he said reaching out to shake the man's hand.

"Good luck out there, Chuck," Harold said.

Chuck got up and began his walk home, Harold watching him leave. Neither man noticed Blair sitting in the window, listening to their entire conversation.

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**REVIEWS ARE LOVE!**


	12. Chapter Twelve

**We've finally reached the end of this story. First, thank you so much to those of you that have stuck with me throughout this story and for the amazing reviews. I'd like to especially thank EZ11 and smartin555, who have reviewed almost every chapter. It means so much to me. Second, I am still debating on an epilogue, although I need some help on ideas so please leave reviews if you want one and let me know what you want to see happen! And third, please check out my new story My Love Will Follow You, which I will be updating a lot more now that this story is done.**

**Thanks again, and enjoy the final chapter of Win A Date With Nate Archibald!**

**I DO NOT OWN GOSSIP GIRL OR WIN A DATE WITH TAD HAMILTON.**

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Chapter Twelve

The next day, after saying goodbye to her father, Blair walked with Serena through the airport following closely behind Nate and his agents. They were on their way out onto the tarmac—Nate had a private plane. Blair had knots in her stomach and was glad that her best friend was there to see her off. Still, someone was missing and she knew it was all her fault. She knew it would never be the same between her and Chuck, even after she came back. She hated that this was the way it had to be.

"B, are you sure you know what you're doing? " Serena asked once they had gotten outside and were standing in front of the plane. Nate and his agents were talking with the pilot, so Serena took this moment alone to talk to her best friend.

"No," Blair answered honestly.

"Have you ever felt more confused or alone?" Serena asked, referring to the Chuck situation. Blair had told her all about it, and although Serena thought it was amazing that Nate Archibald was crazy about her best friend, she still was unsure about what Blair was about to do. She knew Chuck had always loved Blair, and always believed that someday they'd be together. But now, she didn't see that ever happening and it worried her.

"No," she said truthfully.

Serena didn't know what to say. She wanted to be supportive but a large part of her wanted to yell at her and tell her that she was making a huge mistake. But maybe Blair had to learn that for herself.

"Well, have a nice flight."

"Gee, thanks Serena," Blair laughed as she gave her friend a hug.

The two friends walked over to where Nate and his agents were standing and heard the tail end of their conversation.

"So you guys don't mind not flying with us right?" Nate asked them. "I mean, you know, to give us some privacy."

"Of course we don't mind," Richard said with as little sarcasm as possible. He knew he really didn't have a say in the matter.

"Yeah, we're looking forward to our shit-ass commercial flight," Levy added.

"We'll be fine," Richard continued.

"Yeah, I've always wanted to have a layover in Cincinnati," said Levi.

"We'll be absolutely fine—"

"With like another one in Chicago…you know so we'll be in L.A. by, what, April?"

"Alright Levy, that's enough. Really, we'll be fine."

"Okay," Nate interrupted before Levy could make any further complaints. "It's time to go, you ready?" he asked Blair.

"Ready," she smiled back up at him. She turned to give Serena one last hug before following Nate onto the plane.

***

About ten minutes into the flight, Nate got a call on the on-board phone leaving Blair sitting in an armchair towards the front of the plane, looking out the window, her mind buzzing with thoughts.

She couldn't stop thinking about Chuck and how she left things with him. He was her best friend, most of the time a better friend than Serena, and now she was afraid he may never speak to her again. She still couldn't believe that he had kissed her and told her he was in love with her. For some reason, it still wasn't registering how that was possible. She knew she felt something in the kiss, and maybe there would always be something there, but he was too late. She had already made her decision to go with Nate, who she also knew she had feelings for. But she couldn't shake the feeling that she had made a mistake. Chuck was right, she had only known Nate a few days, and while his smiles speech was really sweet, Blair wasn't convinced Nate really knew anything about her.

When she noticed Nate had ended his phone call and was moving back towards the front of the plane, she decided to conduct a small test. She moved to the sideways facing couch of the plane, the same direction she had been sitting in the limo when she got carsick. Nate came and sat in the armchair she had previously been sitting in.

"You okay?" Nate asked when he noticed Blair looking a little uneasy.

"Yeah, I'm just a little nervous, for some reason. I have a little nervous feeling in…myself. But that's only natural right?"

"Well, yeah."

"I mean…this is a pretty huge thing I'm doing. Kind of a great leap of faith. But, I have that faith…in you. So I'm fine. It's going to be great."

"Good."

"Can't you tell by my smile?" she laughed.

Nate smiled quickly before turning to look out the window. Blair noticed this immediately.

"Which one is it?" she asked him sweetly.

"What?" he responded nervously.

"What number smile is it?"

"It's uh…um…1. Smile 1."

Blair looked confused. "No, 1 was when something really made me laugh, right?"

"1 and a half," Nate tried covering.

"Right," Blair said before looking down at her hands folded in her lap, fumbling them nervously.

Nate shifted uncomfortably in his chair before looking back up at her. She looked back at him taking a deep breath before forcing a smile.

"Blair… I didn't know about your six smiles," he confessed. "Chuck told me about them. He made me swear that I wasn't going to break your heart or he would tear me to pieces with his bare hands. I stole the speech from Chuck to get you to come with me. I lied, and I'm sorry. And I know you're probably gonna be really upset, I just—"

Blair couldn't believe what she was hearing.

"So Chuck told you about the six smiles?"

"Yeah…"

"And made you swear that you wouldn't break my heart or he'd tear you to pieces…with his bare hands?" she asked trying to make sense of everything.

"Yeah…"

"That is just so..." Blair didn't know what to call it. It certainly wasn't something she was used to hearing from Chuck Bass. Although…he had called her beautiful, and told her that he was in love with her. _Oh my god, I am the biggest idiot_, she thought.

"That's just so what?" Nate asked breaking her out of her thoughts.

"Adorable," Blair answered as her realization was finally settling in. She was in love with Chuck Bass. Always had been, always will be. She had just been too stupid and too stubborn to realize it until now.

"What?" Nate asked dumbfounded.

"Do you think…it's possible to love someone your whole life and never really realize it until something happens…that makes you see it?"

Nate was beyond confused. "What's that from?"

"No, it's not from anything; I'm just saying it to you."

"Oh," Nate sighed as he finally realized what was happening. She was changing her mind.

Neither of them said anything, not knowing how to handle the situation they found themselves in.

"Wow…what a week," Nate finally said. "Fell in love for the first time…got my heart broken for the first time…was honorable for the first time…got bit in the ass for being honorable for the first time…bought a house…" he rambled laughing at himself along the way.

Blair laughed nervously with him. "I'm sorry…about the broken heart part."

"Yeah," Nate smiled and nodded his head letting her know it was okay. He really had fallen in love with her, but he knew she wasn't in love with him. He wanted her to help him better his life, and he realized that wasn't enough reason to base a relationship on.

Blair smiled back. "Do you think you could take me home now?"

"Yeah," Nate responded a little sadly. "Of course."

***

After saying goodbye to Nate and apologizing again for everything, Blair hailed a cab to take her to Jammin Java. She had to see Chuck.

She hopped out of the cab and ran inside the café and found Serena clearing tables.

"Serena!" she called as she ran over to her.

"Blair!?" Serena exclaimed in surprise as she put down her dishrag.

"Serena, where's Chuck?" she asked pushing past her and making her way towards his office.

"He's not here. Blair, what are you doing here?"

"What do you mean he's not here? He's always here," Blair said panicking.

"No, Blair, he didn't come in today. He drove into the city to look at the new club location. He was going to spend the night there and come back tomorrow to pack up his stuff."

"Well do you have the address of the place? I'll just get on the subway," Blair said.

"Um, yeah he wrote it down…here it is," she said when she found it by the cash register.

"Thank you. I have to go," Blair said before running out of the café without giving Serena any more explanation.

***

Chuck had arrived earlier that day to meet with John Marks at the location he had picked out to be the new Jammin Java. Their meeting went well—John Marks had shown him around and went over how much control Chuck would have in the design, which was almost total control. Chuck was actually getting really excited about the project, despite the hell he had been through in the past week. John had him set up in a hotel for the next two weeks while Chuck looked for an apartment. His life was actually starting to look up, and he was glad he had something to keep his mind off the fact that Blair was off jet-setting with Nate Archibald.

Chuck had stayed behind at the club when John Marks left. He wanted to soak the place in alone, get a few more ideas about what he wanted to do with the place. He switched on an old radio at the end of the bar, sat in one of the barstools and decided to go over the blueprints.

"Hi."

Chuck jumped at the sudden voice, and realizing whose voice it was startled him even more. He slowly turned around in his seat, and sure enough, Blair Waldorf was standing across the room.

Blair was fumbling her hands; she had no idea what to say. She had rejected him less then twenty-four hours ago, and she was extremely nervous at how he would react to her unexpected presence.

Chuck stood up from the barstool to face Blair but didn't say anything. He didn't know what to say. He had no idea what the hell she was doing there. Wasn't she supposed to be in L.A. with her new boyfriend?

Blair opened and closed her mouth about five times debating what to say.

Chuck just stood across from her, his hands in his pockets, waiting for her to make the first move.

"You have five smiles, Chuck," she finally blurted out.

Chuck's face showed a flash of shock and surprise and Blair knew she had him.

"One when you think someone's an idiot. One when you think someone's _really_ an idiot. One when you're working at the café. One when you're trying to be polite. And one…one when you're looking at me." Tears had filled her eyes by the time she got to the last one.

Chuck looked back at her trying to process. He couldn't believe that she had left Nate and was here for him. He wanted to just run up to her and kiss her and hold her, but for some reason all he could think about was the last Nate Archibald movie she had dragged him to see. All he could think about was the music that was currently playing in the background and he recalled the final scene from the movie. He couldn't believe what he was about to do.

Chuck's silence was making Blair feel extremely uneasy. She was too late. He never wanted to see her again, he hated her, he—her thoughts were cut off by his voice finally speaking.

"I can't believe I'm going to say this…but…would you like to dance?"

Blair let out a sharp breath and her face immediately brightened as she broke out into a huge grin. She immediately closed the distance between them, throwing her arms around him when she finally reached him. Chuck immediately wrapped his arms around her back and pulled her as close to him as possible. They swayed back and forth as they kept their close embrace.

Blair pulled back slightly keeping her hands on the back of his neck.

"I love you," she said softly. "I love you so much…and I'm so sorry it took me so long to realize it and I'm such an idiot and—"

Chuck cut off her rant by crashing his lips to hers moving his hands to run through her hair and move to the sides of her face.

He pulled back and looked into her eyes.

"Took you long enough, Waldorf," he teased.

Blair hit his chest playfully and smiled back up at him. "Better late than never, right?"

"Oh, I'd say so," he replied with a smirk, before leaning down to capture her lips once again.

**The end.**

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